- Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues
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A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw
- Hai, Li,Lai, Ruizhi,Lv, Shan,Nie, Ruifang,Wu, Yong,Yang, Zhongzhen,chen, Kang
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- Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions
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A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).
- Xiao, Guorong,Wu, Kaifu,Zhou, Wei,Cai, Qian
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supporting information
p. 4988 - 4991
(2021/10/14)
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- Copper(I)-modified covalent organic framework for CO2 insertion to terminal alkynes
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The carboxylation of terminal alkynes with CO2 is an attractive route for CO2 fixation and conversion, and various homogeneous Cu(I) catalysts have been explored for the reaction. However, it is still a challenge to develop efficient heterogeneous catalysts for the conversion under mild conditions. Considering that covalent organic frameworks (COFs) are emerging as versatile platforms for the design of functional materials, we developed a TpBpy-supported Cu(I) catalyst, where TpBpy is a stable imine-type porous COF furnished with rich N,N- and N,O-chelating sites for Cu(I) immobilization. The hybrid material can efficiently catalyze the conversion of CO2 and terminal alkynes to propiolic acids under relatively mild conditions (1 atm CO2, 60 ℃). The catalytic activity arises from the synergy between the organic framework of TpBpy and the Cu(I) sites. Not merely serving as a porous support to afford isolated and accessible Cu(I) sites, the organic framework itself has its own catalytic activity through the polar and basic N and O functional sites, which could activate the C–H bond and facilitate CO2 absorption. In addition, the framework also serves as a giant ligand to shift the reversible Cu(I)-catalyzed process in favor of carboxylation. The catalyst shows somewhat reduced activity after reused for three cycles owing to the oxidation of Cu(I) to Cu(II), but it can be easily regenerated by treating with KI.
- Bu, Ran,Zhang, Lin,Gao, Lu-Lu,Sun, Weng-Jie,Yang, Shuai-Liang,Gao, En-Qing
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- Pre-carbonized nitrogen-rich polytriazines for the controlled growth of silver nanoparticles: Catalysts for enhanced CO2chemical conversion at atmospheric pressure
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High catalytic activity and sufficient durability are two unavoidable key indices of an efficient heterogeneous catalyst for the direct carboxylation of terminal alkynes with CO2 conversion. Nitrogen-rich covalent triazine frameworks (CTFs) are promising substrates, while random distribution of some residual -NH2 groups brings challenges to the controlled growth of catalytic species. Here, we adopt a pre-carbonization protocol, annealing below the carbonization temperature, to eliminate the random -NH2 groups in CTFs and meanwhile to promote polycondensation degree under the premise of maintaining the pore structure. Benefiting from the improved condensation and orderly N atoms, p-CTF-250, for which CTFs are annealed at 250 °C, exhibits improved CO2 adsorption capacity and the ability to control the growth of Ag NPs. Mono-dispersed Ag NPs are generated controllably and entrapped to form Ag@p-CTF-250 catalysts. These Ag@p-CTF-250 catalysts were employed in the direct carboxylation of various terminal alkynes with CO2 under mild conditions (50 °C, 1 atm) and showed excellent catalytic activity. In addition, these catalysts have robust recyclability and can be used for at least 5 catalytic runs while retaining yield above 90%. CO2 conversion proceeds well under the synergistic effect between the high CO2 capture capability and the uniform tiny Ag NPs in Ag@p-CTF-250 "nanoreactors". The results represent an efficient strategy for controlling the growth of metallic nanoparticles in porous organic polymer substrates containing disordered heteroatoms.
- Liu, Jian,Zhang, Xiaoyi,Wen, Bingyan,Li, Yipei,Wu, Jingjing,Wang, Zhipeng,Wu, Ting,Zhao, Rusong,Yang, Shenghong
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p. 3119 - 3127
(2021/05/25)
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- Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes
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An organocatalytic strategy for the direct carboxylation of terminal alkynes with CO2 has been developed. The combined use of a bifunctional organocatalyst and Cs2CO3 resulted in a robust catalytic system for the preparation of a range of propiolic acid derivatives in high yields with broad substrate scope using CO2 at atmospheric pressure under mild temperatures (60 °C). This work has demonstrated that this organocatalytic method offers a competitive alternative to metal catalysis for the carboxylation of terminal alkynes and CO2. In addition, this protocol was suitable for the three-component carboxylation of terminal alkynes, alkyl halides, and CO2.
- Shi, Jun-Bin,Bu, Qingqing,Liu, Bin-Yuan,Dai, Bin,Liu, Ning
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p. 1850 - 1860
(2021/01/14)
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- An efficient Ag/MIL-100(Fe) catalyst for photothermal conversion of CO2 at ambient temperature
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The conversion of CO2 under mild condition is of great importance because these reactions involving CO2 can not only produce value-added chemicals from abundant and inexpensive CO2 feedstock but also close the carbon cycle. However, the chemical inertness of CO2 requires the development of high-performance catalysts. Herein, Ag nanoparticles/MIL-100(Fe) composites were synthesized by simple impregnation-reduction method and employed as catalysts for the photothermal carboxylation of terminal alkynes with CO2. MIL-100(Fe) could stabilize Ag nanoparticles and prevent them from aggregation during catalytic process. Taking the advantages of photothermal effects and catalytic activities of both Ag nanoparticles and MIL-100(Fe), various aromatic alkynes could be converted to corresponding carboxylic acid products (86%–92% yields) with 1 atm CO2 at room temperature under visible light irradiation when using Ag nanoparticles/MIL-100(Fe) as photothermal catalysts. The catalysts also showed good recyclability with almost no loss of catalytic activity for three consecutive runs. More importantly, the catalytic performance of Ag nanoparticles/MIL-100(Fe) under visible light irradiation at room temperature was comparable to that upon heating, showing that the light source could replace conventional heating method to drive the reaction. This work provided a promising strategy of utilizing solar energy for achieving efficient CO2 conversion to value-added chemicals under mild condition.
- Jing, Peng,Wu, Boyuan,Han, Zongsu,Shi, Wei,Cheng, Peng
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supporting information
p. 3505 - 3508
(2021/05/04)
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- Microwave-assisted fabrication of a mixed-ligand [Cu4(μ3-OH)2]-cluster-based metal–organic framework with coordinatively unsaturated metal sites for carboxylation of terminal alkynes with carbon dioxide
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The development of efficient and stable metal–organic framework (MOF) catalysts with coordinatively unsaturated metal sites for modern organic synthesis is greatly important. Herein, a robust [Cu4(μ3-OH)2]-cluster-based MOF (Cu-MOF) with a mixed-ligand system was successfully fabricated by a microwave-assisted method under mild conditions. The as-prepared Cu-MOF catalyst possessing unsaturated Cu (II) sites exhibited excellent catalytic activity toward the direct carboxylation of 1-ethynylbenzene with CO2, and various propiolic acid derivatives were synthesized in moderate to good yields under optimized reaction conditions. Furthermore, the catalyst remained stable and could be easily recycled for five sequential runs without incredible decrease in catalytic efficiency.
- Wang, Wen-Jing,Sun, Zhong-Hua,Chen, Sheng-Chun,Qian, Jun-Feng,He, Ming-Yang,Chen, Qun
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- Schiff-base molecules and COFs as metal-free catalysts or silver supports for carboxylation of alkynes with CO2
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Carboxylation of terminal alkynes with CO2 to produce propiolic acids is an atom economical and high-value route for CO2 fixation and utilization, but the conversion under mild conditions needs transition metal catalysts. In this article, we demonstrated for the first time the transition-metal-free organocatalysts for the reaction. The efficient catalysts are Schiff bases derived from 1,3,5-triformylphloroglucinol (Tp), either homogeneous (discrete molecules) or heterogeneous (covalent organic frameworks, COFs). The key catalytic sites are phenoxo and imine groups, which activate CO2 through phenoxo-CO2 complexation and also activate the C(sp)-H bond through bifurcate C-H?Nimine and C-H?Ophenoxo hydrogen bonds. The 2,2′-bipyridyl sites in the COF also contribute to the catalytic performance. The COF catalyst is less active than the molecular one but has the advantages of heterogeneous catalysis. Higher performance was also demonstrated by combining silver nanoparticles (AgNPs) with the intrinsically catalytic COF. This work opens up the potential of developing transition-metal-free catalysts for the CO2 conversion reaction and demonstrates the new prospects of COFs as tailorable platforms for heterogeneous catalysis.
- Bu, Ran,Gao, En-Qing,Liu, Xiao-Yan,Mu, Peng-Fei,Zhang, Lin
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supporting information
p. 7620 - 7629
(2021/10/12)
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- Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids
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A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-
- Ghosh, Subhankar,Ghosh, Rajat,Chattopadhyay, Shital K.
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- Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones
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A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.
- Yin, Congcong,Yang, Tao,Pan, Yingmin,Wen, Jialin,Zhang, Xumu
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supporting information
p. 920 - 923
(2020/02/04)
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- Visible light induced 3-position-selective addition of arylpropiolic acids with ethersviaC(sp3)-H functionalization
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Although the 2-position-selective decarboxylative coupling or addition of arylpropiolic acids with cyclic ethers has been intensively investigated, selective functionalization of arylpropiolic acids at the 3-position is still a big challenge. Herein, an i
- Luo, Jun,Wan, Zi-Juan,Yuan, Xiao-Feng
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supporting information
p. 3258 - 3262
(2020/05/14)
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- A Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids
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An iron-catalyzed cascade reaction of radical reduction of allyl alcohols and acetylenic acids to construct polysubstituted α-alkenyl lactones has been developed. In this paper, various allyl alcohols can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramolecular reflex-Michael addition. In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a β-methylene tetrahydrofuran and tetrahydrofuran diene.
- Zhang, Hua,Zhang, Guo-Min,He, Shuai,Shi, Zhi-Chuan,Zhang, Xiao-Mei,Wang, Ji-Yu
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supporting information
p. 8337 - 8344
(2020/11/03)
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- Silver Nanoparticles Architectured HMP as a Recyclable Catalyst for Tetramic Acid and Propiolic Acid Synthesis through CO2 Capture at Atmospheric Pressure
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The recent advancement on the tailored synthesis of hypercrosslinked microporous polymer (HMP-2) has assembled significant concentration by the virtue of its adjustable porosity, operative design and absolutely ordering structure. This perfectly structured Ag NPs supported carbocatalyst (Ag-HMP-2) has been synthesized by Friedel-Crafts alkylation between 4,4′-Bis(bromomethyl)-1,1′-biphenyl and carbazole over anhydrous iron(III)chloride catalysis followed by the appending of the silver nanoparticles (Ag NPs) onto the material. The silver nanoparticle was decorated over the HMP-2 to prepare the corresponding catalyst (Ag-HMP-2). The characterization of the newly produced material has been conducted by N2 adsorption/desorption studies, XPS, FE-SEM, transmission electron microscopy (TEM) and Powder X-ray diffraction (PXRD) methods. This microporous catalyst has spectacular activities for the production of tetramic acids from various types of propargylic amine derivatives at 60 °C under atmospheric carbon dioxide pressure. Parallel attempt on fixation of CO2 was executed over terminal alkynes to synthesize propiolic acids under 1 atm pressure. The catalyst (Ag-HMP-2) exhibited sufficient recycling ability for the generation of tetramic acids and propiolic acids up to five catalytic runs without reduction in its catalytic activity.
- Ghosh, Swarbhanu,Ghosh, Aniruddha,Riyajuddin, Sk,Sarkar, Somnath,Chowdhury, Arpita Hazra,Ghosh, Kaushik,Islam, Sk. Manirul
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p. 1055 - 1067
(2020/01/21)
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- Alkynylboration Reaction Leading to Boron-Containing π-Extended cis-Stilbenes as a Highly Tunable Fluorophore
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An unprecedented boron-containing fluorophore, π-extended cis-stilbene, obtained via alkynylboration reaction of alkynamide is reported. Boron-containing π-extended cis-stilbenes emit fluorescence with high quantum yields in the solid state and exhibit aggregation-induced emission enhancement. The broad substrate scope of the alkynylboration reaction offers facile access to electronically diverse structures, enabling fine-tuning of light absorption/emission characteristics. The boron-containing π-extended cis-stilbene with a diphenylamino group displays solvatofluorochromism via an intramolecular charge-transfer transition.
- Nogami, Marina,Hirano, Keiichi,Morimoto, Kensuke,Tanioka, Masaru,Miyamoto, Kazunori,Muranaka, Atsuya,Uchiyama, Masanobu
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supporting information
p. 3392 - 3395
(2019/05/10)
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- Gold(i)-catalyzed pathway-switchable tandem cycloisomerizations to indolizino[8,7-: B] indole and indolo[2,3-a] quinolizine derivatives
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Experimental and theoretical explorations were performed on the pathways of the cascade cycloisomerizations of tryptamine-N-ethynylpropiolamide substrates. The methodology provided a common strategy to access either indolizino[8,7-b]indoles or indolo[2,3-
- Liu, Chengjun,Sun, Zenghui,Xie, Fukai,Liang, Guoduan,Yang, Lu,Li, Yaqiao,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
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p. 14418 - 14421
(2019/12/05)
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- NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers
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A direct alkenylation of cyclic ethers via radical cross decarboxylative coupling process catalyzed by NiCl2 and using DTBP as radical initiator and oxidant was developed. A variety of arylpropiolic acids and cyclic ethers were transformed into the corresponding 2-arylvinyl cyclic ethers in moderate to excellent yields. Mechanistic experiments were conducted to determine the nature of the reaction intermediates, and a plausible reaction mechanism involving NiCl2-promoted radical process was proposed.
- Wan, Zi-juan,Wang, Jin-yuan,Luo, Jun
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supporting information
p. 613 - 616
(2019/01/29)
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- Rhodium(III)-catalysed cascade [3 + 2] annulation of: N -aryloxyacetamides with 3-(hetero)arylpropiolic acids: Synthesis of benzofuran-2(3 H)-ones
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Herein, a cascade [3 + 2] annulation of N-aryloxyacetamides with 3-(hetero)arylpropiolic acids affording benzofuran-2(3H)-ones via rhodium(iii)-catalyzed redox-neutral C-H functionalization/isomerization/lactonization using an internal oxidative directing group O-NHAc was achieved. This catalytic system provides a regio- and stereoselective approach to synthesize (Z)-3-(amino(aryl)methylene)benzofuran-2(3H)-ones with exclusive Z configuration selectivity, acceptable yields and good functional group tolerance. Preliminary investigations on ultraviolet-visible and fluorescence behaviors reveal that the annulation products may be applied as a promising fluorescent probe for sensing metal cations, especially for cerium (Ce3+).
- Pan, Jin-Long,Liu, Tuan-Qing,Chen, Chao,Li, Quan-Zhe,Jiang, Wei,Ding, Tong-Mei,Yan, Zhi-Qiang,Zhu, Guo-Dong
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supporting information
p. 8589 - 8600
(2019/10/02)
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- Visible-light-mediated selective thiocyanation/ipso-cyclization/oxidation cascade for the synthesis of thiocyanato-containing azaspirotrienediones
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A visible-light-mediated metal-free thiocyanate radical addition/ipso-cyclization/oxidation cascade reaction for the synthesis of thiocyanato-containing azaspirotrienediones from N-phenylpropynamides is described. Cheap and readily available ammonium thiocyanate was used as a precursor to the thiocyanate free radical, which undergoes a radical addition reaction with the alkyne, followed by selective ipso-cyclization and oxidation to afford the dearomatized products. No product of ortho-cyclization was detected. The reaction completes the synthesis of C–S, C–C, and C[dbnd]O bonds in one pot, with abundant and renewable air oxygen as the sole sacrificial reagent and oxygen source.
- Chen, Yuan,Chen, Yu-Jue,Guan, Zhi,He, Yan-Hong
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supporting information
(2019/11/26)
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- Porous Carbon Nitride Frameworks Derived from Covalent Triazine Framework Anchored Ag Nanoparticles for Catalytic CO2 Conversion
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Porous carbon nitride frameworks (PCNFs) with uniform and rich nitrogen dopants and abundant porosity were successfully fabricated through the direct carbonization of the covalent triazine frameworks (CTFs) at different pyrolysis temperatures and used as supports to anchor and stabilize Ag nanoparticles (NPs) for catalytic CO2 conversion. Importantly, the pyrolysis temperature plays a crucial role in the properties of porous carbon nitride frameworks. The material carbonized at 700 °C showed the highest surface area and micro- and mesoporous structure with a certain interlayer distance. Taking advantage of their unique surface characteristics, PCNF-supported Ag NP catalysts (Ag/PCNF-T, T=pyrolysis temperature) were prepared by a simple chemical method. A series of characterizations revealed that Ag NPs are embedded in the porous carbon nitride frameworks and confined to a relatively small size with high dispersion owing to the assistance of the abundant surface groups and porous structures. The as-obtained Ag/PCNF-T catalysts, especially Ag/PCNF-700, showed excellent catalytic activity, selectivity, and stability for the carboxylation of CO2 with terminal alkynes under mild conditions. This can be due to the existence of abundant nitrogen atoms and diverse porosity, which resulted in highly efficient catalytic activity and stability.
- Lan, Xingwang,Li, Yiming,Du, Cheng,She, Tiantian,Li, Qing,Bai, Guoyi
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supporting information
p. 8560 - 8569
(2019/06/08)
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- Fixation of CO2 as a carboxylic acid precursor by microcrystalline cellulose (MCC) supported Ag NPs: A more efficient, sustainable, biodegradable and eco-friendly catalyst
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Silver nanoparticles supported on microcrystalline cellulose (Ag NPs@MCC), an active catalyst, has been discovered for the direct carbonylation of terminal alkynes with CO2 into carboxylic acid under mild and sustainable reaction conditions. The stabilized Ag NPs show higher distribution with a uniform particle size. The catalyst was characterized by PXRD, SEM, TEM, HR-TEM, EDS, EDX, ICP-AES and XPS analysis. The Ag NPs@MCC material was found to be more efficient, shows excellent dispersion in various solvents and is biodegradable. The solvent effects on carbonylation of terminal alkynes were well studied both experimentally and computationally. Furthermore, the present catalyst can be recycled in up to five catalytic cycles without significant loss of its activity and is also applicable for the gram scale carbonylation of terminal alkynes.
- Shah, Dharmesh J.,Sharma, Anuj S.,Shah, Akshara P.,Sharma, Vinay S.,Athar, Mohd,Soni, Jigar Y.
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supporting information
p. 8669 - 8676
(2019/06/14)
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- Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence
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A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.
- Verma, Astha,Grams, R. Justin,Rastatter, Brett P.,Santos, Webster L.
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p. 2113 - 2117
(2019/02/25)
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- Acetylene and terminal alkyne complexes of copper(i) supported by fluorinated pyrazolates: Syntheses, structures, and transformations
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Trinuclear {μ-[3,5-(CF3)2Pz]Cu}3 reacts with acetylene to produce the 2:1 copper(i) acetylene complex, Cu4(μ-[3,5-(CF3)2Pz])4(μ-HCCH)2. Related Cu4(μ-[4-Br-3,5-(CF3)2Pz])4(μ-HCCH)2 and Cu4(μ-[4-Cl-3,5-(CF3)2Pz])4(μ-HCCH)2 have also been isolated using the corresponding copper(i) pyrazolate and acetylene. The 1:1 adducts Cu2(μ-[3,5-(CF3)2Pz])2(HCCH)2 and Cu2(μ-[4-Br-3,5-(CF3)2Pz])2(HCCH)2 are significantly less stable to the acetylene loss and can be observed in solution at low temperatures under excess acetylene. The X-ray crystal structures of 2:1 and 1:1 complexes, Cu4(μ-[3,5-(CF3)2Pz])4(μ-HCCH)2 and Cu2(μ-[4-Br-3,5-(CF3)2Pz])2(HCCH)2 are reported. Raman data show a reduction in CC stretching frequency by about ~340 and ~163 cm-1 in the 2:1 and 1:1 Cu(i)/acetylene complexes, respectively, from that of the free acetylene. Copper(i) pyrazolate complexes of the terminal alkynes, phenylacetylene, 1,8-nonadiyne, and 1,7-octadiyne are also reported. They form adducts involving one copper atom on each alkyne moiety. The {μ-[3,5-(CF3)2Pz]Cu}3 is also a very versatile and competent catalyst for alkyne transformations as evident from its ability to catalyze the alkyne C(sp)-H bond carboxylation chemistry with CO2, azide-alkyne cycloadditions leading to 1,2,3-triazoles including the use of acetylene itself as a substrate, and thiol addition to phenylacetylene affording vinyl sulfides.
- Parasar, Devaborniny,Ponduru, Tharun T.,Noonikara-Poyil, Anurag,Jayaratna, Naleen B.,Dias, H.V. Rasika
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p. 15782 - 15794
(2019/11/11)
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- Gold-Catalyzed Post-Ugi Cascade Transformation for the Synthesis of 2-Pyridones
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A gold-catalyzed post-Ugi cascade transformation for the synthesis of 2-pyridones is described. The process involves furan–alkyne cyclization followed by furan ring-opening and cleavage of the isocyanide-originated fragment. The initially formed cis double bond can isomerize into a more stable trans double bond upon prolonged exposure to a strong Br?nsted acid. Thus, the overall strategy provides a viable access towards two types of 2-pyridones.
- Du, Xiaochen,Yu, Jiafeng,Gong, Jing,Zaman, Manzoor,Pereshivko, Olga P.,Peshkov, Vsevolod A.
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supporting information
p. 2502 - 2507
(2019/04/08)
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- Rhodium-catalyzed enantioselective decarboxylative alkynylation of allenes with arylpropiolic acids
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A rhodium-catalyzed chemo-, regio-, and enantioselective intermolecular decarboxylative alkynylation of terminal allenes with arylpropiolic acids is reported. Employing a Rh(I)/(R)-Tol-BINAP catalytic system, branched allylic 1,4-enynes were obtained under mild conditions. The overall utility of this protocol is exemplified by a broad functional group compatibility.
- Grugel, Christian P.,Breit, Bernhard
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supporting information
p. 1066 - 1069
(2018/02/23)
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- Synthesis and antibacterial evaluation of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives
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A series of novel 11-O-aralkylcarbamoyl-3-O-descladinosylclarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activity. The results showed that the majority of the target compounds displayed potent activity against erythromycin-susceptible S. pyogenes, erythromycin-resistant S. pneumoniae A22072 expressing the mef gene and S. pneumoniae AB11 expressing the mef and erm genes. Besides, most of the target compounds exhibited moderate activity against erythromycin-susceptible S. aureus ATCC25923 and B. subtilis ATCC9372. In particular, compounds 11a, 11b, 11c, 11e, 11f and 11h were found to exert favorable antibacterial activity against erythromycin-susceptible S. pyogenes with the MIC values of 0.015–0.125 μg/mL. Furthermore, compounds 10e, 11a, 11b and 11c showed superior activity against erythromycin-resistant S. pneumoniae A22072 with the MIC values of 0.25–0.5 μg/mL. Additionally, compound 11c was the most effective against all the erythromycin-resistant S. pneumoniae strains (A22072, B1 and AB11), exhibiting 8-, 8- and 32-fold more potent activity than clarithromycin, respectively.
- Jia, Li,Wang, Yinhu,Wang, Yanxia,Qin, Yinhui,Hu, Chaoyu,Sheng, Juzheng,Ma, Shutao
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p. 2471 - 2476
(2018/06/06)
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- Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
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Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
- Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
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p. 1218 - 1231
(2018/02/16)
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- Method for synthesizing alpha-alkynyl substituted ether compounds
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The invention discloses a method for preparing alpha-alkynyl substituted ether compounds. The method comprises the following steps: taking propiolic acid as a raw material, and synthesizing substituted phenylpropiolic acid under conditions of substituted iodobenzene, 1,8-diazabicyclo[5.4.0]undec-7-ene, (beta-4)-platinu and dimethyl sulfoxide; taking substituted phenylpropiolic acid and p-bromophenol as raw materials, and synthesizing p-bromophenyl substituted phenylpropiolic acid ester under the conditions of 4-dimethylaminopyridine and N,N'-Dicyclohexylcarbodiimide; and performing an alkynylation reaction on the p-bromophenyl substituted phenylpropiolic acid ester in participation of tert-butyl hydroperoxide, cesium carbonate and tetrahydrofuran, and finally synthesizing alpha-alkynyl substituted ether products. According to the method disclosed by the invention, simple and readily available acetylene esters serve as an alkynylation reagent, and the target products, namely alpha-alkynyl substituted ether compounds, are synthesized in a green and environmental-friendly manner under mild conditions. The compounds play an important role in construction of multiple medical intermediates and bio-active structures.
- -
-
Paragraph 0029; 0031
(2018/04/01)
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- Sequential protocol for C(sp)–H carboxylation with CO2: KOtBu-catalyzed C(sp)–H silylation and KOtBu-mediated carboxylation
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CO2 incorporation into C–H bonds is an important and interesting topic. Herein a sequential protocol for C(sp)–H carboxylation by employing a metal-free C–H activation/catalytic silylation reaction in conjunction with KOtBu-mediated carboxylation with CO2 was established, in which KOtBu catalyzes silylation of terminal alkynes to form alkynylsilanes at low temperature, and simultaneously mediates carboxylation of the alkynesilanes with atmospheric CO2. Importantly, the carboxylation further promotes the silylation, which makes the whole reaction proceed very rapidly. Moreover, this methodology is simple and scalable, which is characterized by short reaction time, wide substrate scope, excellent functional-group tolerance and mild reaction conditions, affording a range of corresponding propiolic acid products in excellent yields in most cases. In addition, it also allows for a convenient 13C-labeling through the use of 13CO2.
- Yu, Bo,Yang, Peng,Gao, Xiang,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Liu, Zhimin
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p. 449 - 456
(2018/02/06)
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- Binuclear molybdenum alkoxide as the versatile catalyst for the conversion of carbon dioxide
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The triply bonded dimolybdenum compound, Mo2(OtBu)6 (1), was investigated as a homogeneous catalyst for the conversion of CO2. The compound 1 acted as a rare example of a versatile catalyst with an impressive ability to transform CO2 into various valuable products, including propiolic acids, cyclic carbonates, and benzo[d]thiazole- and benzo[d]oxazolecarboxylic acids, in high yields with short reaction times and excellent selectivity at ambient pressure and low temperatures (25-75 °C). This is the first report of the application of a metal-metal bond-containing species in the catalytic conversion of CO2.
- Chen, Jing-Huo,Deng, Cheng-Hua,Fang, Sheng,Ma, Jian-Gong,Cheng, Peng
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p. 989 - 996
(2018/03/13)
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- Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
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A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
- Cui, Fei-Hu,Chen, Jing,Mo, Zu-Yu,Su, Shi-Xia,Chen, Yan-Yan,Ma, Xian-Li,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming,Xu, Yan-Li
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supporting information
p. 925 - 929
(2018/02/22)
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- Central Doping of a Foreign Atom into the Silver Cluster for Catalytic Conversion of CO2 toward C?C Bond Formation
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Clusters with an exact number of atoms are of particular interest in catalysis. Their catalytic behaviors can be potentially altered with the addition or removal of a single atom. Now the effects of doping with a single foreign atom (Au, Pd, and Pt) into the core of an Ag cluster with 25 atoms on the catalytic properties are explored, where the foreign atom is protected by 24 Ag atoms (Au@Ag24, Pd@Ag24, and Pt@Ag24). The central doping of a single atom into the Ag25 cluster has a substantial influence on the catalytic performance in the carboxylation reaction of CO2 with terminal alkyne through C?C bond formation to produce propiolic acid. These studies reveal that the catalytic properties of the cluster catalysts can be dramatically changed with the subtle alteration by a single atom away from the active sites.
- Liu, Yuanyuan,Chai, Xiaoqi,Cai, Xiao,Chen, Mingyang,Jin, Rongchao,Ding, Weiping,Zhu, Yan
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supporting information
p. 9775 - 9779
(2018/07/31)
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- Rational encapsulation of atomically precise nanoclusters into metal-organic frameworks by electrostatic attraction for CO2 conversion
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Controlled encapsulation of atomically precise nanoclusters (APNCs) into metal-organic frameworks (MOFs) has been an efficient way to create new types of multifunctional crystalline porous materials. Such hybrids (APNCs@MOFs) provide ideal candidates for studying inherent structure-catalysis relationships owing to the well-defined compositions of both components. Moreover, modeling of APNCs@MOFs with precise structures would be more reliable. Herein, we have established an "Electrostatic Attraction Strategy" to synthesize APNCs@MOF catalysts and studied their performance as catalysts for the conversion of CO2. The synthetic strategy presented here has been proved to be general, as evidenced by the syntheses of various APNCs@MOF catalysts including all the combinations of [Au12Ag32(SR)30]4-, [Ag44(SR)30]4-, and [Ag12Cu28(SR)30]4- nanoclusters with ZIF-8, ZIF-67, and MHCF frameworks. In particular, the as-obtained Au12Ag32(SR)30@ZIF-8 composite shows excellent performance in capturing CO2 and converting phenylacetylene into phenylpropiolate under mild conditions (50 °C and ambient CO2 pressure) with a TON as high as 18164, far exceeding those of most known catalysts. What's more, the catalyst is very stable and reused 5 times without loss of catalytic activity. We anticipate that this general synthetic approach may open up a new frontier in the development of promising APNCs@MOF catalysts, which can be applied in a broad range of heterogeneous catalyses in the future.
- Sun, Lili,Yun, Yapei,Sheng, Hongting,Du, Yuanxin,Ding, Yimin,Wu, Pei,Li, Peng,Zhu, Manzhou
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supporting information
p. 15371 - 15376
(2018/08/17)
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- Method for preparing propiolic acid and derivatives thereof under mild condition
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The invention provides a novel method for preparing propiolic acid compounds through a domino reaction. The method comprises a step of subjecting terminal alkyne compounds, hydrosilane and CO2 to thedomino reaction under the catalysis action of Lewis base so as to obtain propiolic acid compounds. According to the invention, common Lewis base is used as a promoter, and corresponding propiolic acidcompounds containing different function groups can be efficiently produced through a reaction of the terminal alkyne compounds with hydrosilane and normal-pressure CO2 under a mild condition (a temperature of 40 DEG D). According to the method, CO2 is used as a raw material; the cheap Lewis base is used as the promoter; usage of precious metals is avoided; the domino reaction is employed; purification and separation of intermediates are not needed; and reaction conditions are mild. Thus, the method is an efficient cheap green synthetic method and has good industrial application value.
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Paragraph 0027; 0028; 0077; 0078
(2018/09/08)
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- Carbene-catalyzed LUMO activation of alkyne esters for access to functional pyridines
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A carbene-catalyzed LUMO activation of α,β-unsaturated alkyne esters is reported. This catalytic process allows for effective reactions of alkyne esters with enamides to synthesize functional pyridines via simple protocols. A previously unexplored unsaturated alkyne acyl azolium intermediate is involved in the key step of the reaction.
- Mou, Chengli,Wu, Jichang,Huang, Zhijian,Sun, Jun,Jin, Zhichao,Chi, Yonggui Robin
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supporting information
p. 13359 - 13362
(2017/12/26)
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- Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles
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Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.
- Sahani, Rajkumar Lalji,Liu, Rai-Shung
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supporting information
p. 1026 - 1030
(2017/01/18)
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- Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent
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A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.
- Kadari, Lingaswamy,Palakodety, Radha Krishna,Yallapragada, Lakshmi Prapurna
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supporting information
p. 2580 - 2583
(2017/05/24)
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- Copper-Catalyzed, Stereoselective Bis-trifluoromethylthiolation of Propiolic Acid Derivatives with AgSCF3
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A copper-catalyzed chemo- and stereoselective oxidative bis-trifluoromethylthiolation of propiolic acid derivatives was achieved by using carboxylic acid as the activating group and formic acid as a cosolvent. The reaction of propiolic acid derivatives and AgSCF3 in the presence of (NH4)2S2O8 and catalytic Cu(OAc)2 in MeCN/HCO2H afforded bis-trifluoromethylthiolated acrylic acids in moderate to excellent yields with E selectivity. Further derivatization of the resultant products gave a series of polysubstituted SCF3-containing alkenes.
- Pan, Shen,Li, Huan,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
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supporting information
p. 3247 - 3250
(2017/06/23)
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- Tandem trifluoromethylthiolation/aryl migration of aryl alkynoates to trifluoromethylthiolated alkenes
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A trifluoromethylthiolation initiated aryl migration of aryl alkynoates was disclosed. This protocol employs AgSCF3 as the SCF3 source and MeCN as both the solvent and the hydrogen source. This provides a new access to trifluoromethylthiolated alkenes from readily available substrates and reagents.
- Li, Huan,Liu, Shuai,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
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supporting information
p. 10136 - 10139
(2017/09/23)
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- Composite System of Ag Nanoparticles and Metal-Organic Frameworks for the Capture and Conversion of Carbon Dioxide under Mild Conditions
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The materials Ag@MIL-100(Fe) and Ag@UIO-66(Zr) are obtained for the capture and transformation of CO2 into alkynyl carboxylic acids, which are environmental friendly, facile to synthesize, and exhibit excellent efficiency and reusability. The influence on the catalytic activity of such Ag@MOF systems by metal-organic frameworks' (MOFs) surface area, thermal, and chemical stability, especially the acid-base characteristics of the pores, are compared and discussed systematically.
- Zhu, Ning-Ning,Liu, Xiao-Huan,Li, Tao,Ma, Jian-Gong,Cheng, Peng,Yang, Guang-Ming
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supporting information
p. 3414 - 3420
(2017/03/24)
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- Cis -1,2-Bis(diphenylphosphino)ethylene copper(i) catalyzed C-H activation and carboxylation of terminal alkynes
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The reaction of cis-1,2-bis(diphenylphosphino)ethylene (dppet) with CuX (X = CN, SCN) in 1:1 M molar ratio in DCM-MeOH (50:50 V/V) under refluxing conditions gave two dimeric Cu(i) complexes, viz. [Cu2(μ-CN)2(κ2-P,P-dppet)2] (1) and [Cu2(μ2-SCN)2(κ2-P,P-dppet)2] (2). These complexes have been characterized by elemental analyses, IR, 1H and 31P NMR, and electronic absorption spectroscopies, and ESI-MS. The molecular structure of 2 was confirmed by single crystal X-ray diffraction, which indicated that 2 exists as a centrosymmetric dimer in which the two copper centers are bonded to two dppet ligands and two bridging thiocyanate groups in a μ2-manner. The electrochemical properties of 1 and 2 were studied by cyclic voltammetry. Both the complexes exhibited strong luminescence properties in the solution state at ambient temperature. Both the complexes were found to be efficient catalysts for the conversion of terminal alkynes into propiolic acids with CO2. Owing to their excellent catalytic activity, the reactions proceed at atmospheric pressure and ambient temperature (25 °C). The catalytic products were obtained in excellent yields (90-97%) by using the complex loading of 1 mol%.
- Trivedi, Manoj,Smreker, Jacob R.,Singh, Gurmeet,Kumar, Abhinav,Rath, Nigam P.
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p. 14145 - 14151
(2017/11/28)
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- CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 at room temperature
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A CsF-promoted carboxylation of aryl(hetaryl) terminal alkynes with atmospheric CO2 in the presence of trimethylsilylacetylene was developed to give functionalized propiolic acid products at room temperature. A wide range of propiolic acids bearing functional groups was successfully obtained in good to excellent yields. Mechanistic studies demonstrate that in the carboxylation process the alkynylsilane intermediate was first in situ generated, which was then trapped by CO2, giving rise to the corresponding functionalized propiolic acids after acidification. The advantages of this approach include avoiding use of transition-metal catalysts, wide substrate scope together with excellent functional group tolerance, ambient conditions and a facile work-up procedure.
- Yu,Yang,Gao,Yang,Zhao,Zhang,Liu
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supporting information
p. 9250 - 9255
(2017/08/29)
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- Preparation method of propiolic acid compounds
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The invention relates to CO2 activation and conversion and related chemical technical fields, and specifically relates to a synthesis method of propiolic acid compounds. The method is characterized in that in the presence of an added additive and alkalis, terminal alkynes directly react with CO2 to generate propiolic acid compounds. The proper terminal alkyne substrate may be phenyl acetylene, substituted phenyl acetylene, heterocyclic aryl alkynes, or aliphatic terminal alkynes. Compared with the prior art, the invention mainly provides a novel and simple reaction system. According to the preparation method, potassium carbonate is taken as the alkali, quaternary ammonium salts are taken as the additive, and acetonitrile, which is convenient for the post treatment, is taken as the solvent. The preparation method is reported for the first time. The reaction system does not need any transition metal catalyst; the experiment operation is simple; the raw materials are cheap and easily available, and the preparation method is environment-friendly and generates great application value, social benefits, and economic benefits.
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Paragraph 0046-0048
(2017/10/12)
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- Preparation method of propiolic acid compounds
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The invention belongs to the technical fields of carbon dioxide activation and conversion and related chemistry, and discloses a preparation method of propiolic acid compounds. The preparation method comprises the following steps: (1) adding a copper catalyst, an additive, an alkali, and solid terminal alkynes into a reactor, adding an organic solvent under the protection of nitrogen gas, and filling CO2 into the reactor; or adding a copper catalyst, an additive, and an alkali into a reactor, adding an organic solvent and liquid terminal alkynes, and filling CO2 into the reactor; (2) sealing the reactor, and placing the reactor in an oil bath to carry out reactions; and (3) after reactions, opening a valve of the reactor to slowly release residual gas in the reactor, transferring the reaction liquid to a one-mouth bottle, carrying out concentration, diluting the concentrate by deionized water, adding n-hexane to carry out extraction, adding hydrochloric acid to carry out acidification, adding diethyl ether to carry out extraction, collecting the organic phase, washing the organic phase by a saturated saline solution, drying the organic phase by anhydrous sodium sulfate, filtering, and removing the solvent in vacuum to obtain the target material. The preparation method has the advantages of low reaction cost, simple experiment operation, mild reaction conditions, and easiness for industrialization.
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Paragraph 0043; 0044; 0045
(2017/12/09)
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- Substrate-Assisted, Transition-Metal-Free Diboration of Alkynamides with Mixed Diboron: Regio- and Stereoselective Access to trans-1,2-Vinyldiboronates
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A substrate-assisted diboration of alkynamides using the unsymmetrical pinacolato-1,8-diaminonaphthalenato diboron (pinBBdan) is described. The transition-metal-free reaction proceeds in a regio- and stereoselective fashion to exclusively afford trans-vinyldiboronates in good to excellent yields. Notably, Bdan and Bpin are installed on the α- and β-carbon atoms, respectively.
- Verma, Astha,Snead, Russell F.,Dai, Yumin,Slebodnick, Carla,Yang, Yinuo,Yu, Haizhu,Yao, Fu,Santos, Webster L.
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supporting information
p. 5111 - 5115
(2017/04/24)
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- Synthesis of Terminal Allenes via a Copper-Catalyzed Decarboxylative Coupling Reaction of Alkynyl Carboxylic Acids
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Synthesis of terminal allenes via a copper-catalyzed decarboxylative coupling reaction was developed. Aryl alkynyl carboxylic acid, paraformaldehyde, and dicyclohexylamine were reacted with CuI (20 mol %) in diglyme at 100°C for 2 h to produce the terminal allene in moderate to good yields. The method showed good functional group tolerance.
- Lim, Jeongah,Choi, Jinseop,Kim, Han-Sung,Kim, In Seon,Nam, Kye Chun,Kim, Jimin,Lee, Sunwoo
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p. 303 - 308
(2016/01/15)
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- Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3at room temperature
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A novel Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3has been developed for the construction of Csp-CF3bond under mild conditions. This method proceeds smoothly at room temperature and shows a widely functional compatibility, providing a series of corresponding trifluoromethylated acetylenyl-containing aromatics in good yields.
- Yang, Lingling,Jiang, Linlin,Li, Yaming,Fu, Xinmei,Zhang, Rong,Jin, Kun,Duan, Chunying
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p. 3858 - 3862
(2016/07/06)
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- Method for preparing propiolic acid compounds
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The invention discloses a method for preparing propiolic acid compounds. An ionic type iron (III) complex containing monoimide functionalized imidazolium cations is taken as the single-component catalyst, carbon dioxide is taken as the carboxylation reagent, and various propiolic acid compounds are prepared through carboxylation reaction of terminal alkyne under normal pressure. The terminal alkyne substrate relates to phenylacetylene, substituted phenylacetylene, heterocyclic aryne, aromatic diyne or aliphatic series terminal alkyne. The method for preparing the propiolic acid compounds through carboxylation reaction of terminal alkyne and carbon dioxide under the catalysis of the iron-based catalyst is provided for the first time. Compared with the prior art, the method has the advantages that the catalyst is more environmentally friendly, synthesis is easier, reaction conditions are mild, and catalytic activity and functional group tolerance are unchanged or improved.
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Paragraph 0032; 0033
(2016/10/10)
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- A bridged bis-amide-based rare earth amine compound and its preparation method and application
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The invention discloses bridged bisamido rare-earth amide compounds, and a preparation method and catalytic application thereof. The general formula of the rare-earth compounds is {LLn[N(SiMe3)2].THF}2, and the chemical structural formula is disclosed in the specification. In the general formula, L represents a bridged bisamido ligand, and the ligand LH2 is N,N'-(cyclohexane-1,2-diyl)bis(4-tert-butylbenzamide); and Ln is a rare-earth metal selected from lanthanum, neodymium, samarium, yttrium or ytterbium. The bridged bisamido rare-earth amide compounds have the advantages of simple synthesis process, definite structure and high yield. The invention also discloses a preparation method of the compounds and an application method of the compounds as a catalyst for catalyzing carboxylation reaction between alkynyl terminal group and carbon dioxide. The application method has the advantages of mild conditions, high activity, favorable selectivity and wide substrate application range.
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Paragraph 0115; 0116
(2017/04/21)
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- Carboxylation of terminal alkynes with CO2 using novel silver N-heterocyclic carbene complexes
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Four novel N-heterocyclic carbene (NHC) silver complexes, I-IV, have been synthesized and characterized. The single X-ray crystal diffraction data indicate a dinuclear solid-state structure for I and III and a mononuclear structure for II and IV. These complexes have been successfully used as efficient catalysts for the C-H activating carboxylation of terminal alkynes with CO2. A wide range of substrates with various functional groups afforded the corresponding aryl or alkyl substituted propiolic acids in good yields under mild conditions. Moreover, the role of bases and the reaction mechanism is thoroughly discussed.
- Li, Shanshan,Sun, Jing,Zhang, Zhizhi,Xie, Ruixia,Fang, Xiangchen,Zhou, Mingdong
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p. 10577 - 10584
(2016/07/07)
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- Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives
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Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.
- Karad, Somnath Narayan,Chung, Wei-Kang,Liu, Rai-Shung
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supporting information
p. 13004 - 13007
(2015/08/06)
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