- Copper-Catalyzed Aerobic Oxidative Cyclization of 2-Alkynylanilines with Nitrosoarenes: Synthesis of Organic Solid Mechanoluminescence Compounds of 4-Oxo-4 H-cinnolin-2-ium-1-ide
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An efficient Cu(I)/DMAP/air system for the one-pot synthesis of 4-oxo-4H-cinnolin-2-ium-1-ides, which are often difficult to prepare by traditional routes from substituted 2-alkynylanilines and nitrosoarenes, was developed. These 4-oxo-4H-cinnolin-2-ium-1-ides have practical applications as mechanoluminescent materials. Preliminary mechanistic experiments were performed, and a plausible mechanism for this tandem process is proposed. The use of an inexpensive copper catalyst and molecular oxygen as the oxygen source and the oxidant make this an attractive green protocol with potential synthetic applications.
- Fang, Xiaolan,Cao, Ji,Ding, Weijie,Jin, Huile,Yu, Xiaochun,Wang, Shun
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supporting information
p. 1228 - 1233
(2021/02/20)
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- Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens
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A Cu(I)-mediated cascade cyclization/annulation of unprotectedo-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ~17 ns. The annulated3aadisplays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.
- Khandelia, Tamanna,Ghosh, Subhendu,Panigrahi, Pritishree,Shome, Rajib,Ghosh, Siddhartha Sankar,Patel, Bhisma K.
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p. 16948 - 16964
(2021/12/02)
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- Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds
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Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e
- Lv, Jiahang,Zhao, Binlin,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
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supporting information
p. 691 - 694
(2020/07/13)
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- Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides
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N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.
- de Souza, Wanderson C.,Matsuo, Bianca T.,Matos, Priscilla M.,Correia, José Tiago M.,Santos, Marilia S.,K?nig, Burkhard,Paix?o, Marcio W.
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supporting information
p. 3722 - 3728
(2021/02/03)
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- Gold(I)-Catalyzed Reactions between N-(o-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1 H-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates
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This work describes gold-catalyzed additions of vinyldiazo ketones to N-(o-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1H-indoles involving skeletal rearrangement; these new catalytic reactions are applicable to a wide range of substrates. We postu
- Kulandai Raj, Antony Sekar,Narode, Akshay Subhash,Liu, Rai-Shung
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supporting information
p. 1378 - 1382
(2021/03/03)
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- Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused γ-Lactones fromN-(o-Ethynylaryl)acrylamides and Formamide
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An ultrafast (10 s) methodology to construct novel highly functionalized 2-quinolinones fromN-(o-ethynylaryl)acrylamides (1,7-enynes) is described for the first time. Microwave irradiation enabled the ultrafast synthesis of 2-quinolinone-fused γ-lactones from Fenton’s reagents in formamide. After six key consecutive reactions, including a diastereoselective step, 2-quinolinone-fused γ-lactones were obtained in good overall yield (up to 46%; 10 s).
- Sacchelli, Bruce A. L.,Rocha, Bianca C.,Andrade, Leandro H.
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supporting information
p. 5071 - 5075
(2021/07/20)
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- Asymmetric Synthesis of 3-Methyleneindolines via Rhodium(I)-Catalyzed Alkynylative Cyclization of N-(o-Alkynylaryl)imines
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The first asymmetric synthesis of 3-methyleneindolines from alkynyl imines has been developed via a rhodium-catalyzed tandem process: regioselective alkynylation of the internal alkynes and subsequent intramolecular addition to the imines. The reaction pr
- Yuan, Shi-Yi,Yan, Qi-Qi,Wang, Dan,Dan, Ting-Ting,He, Long,He, Cheng-Yu,Chu, Wen-Dao,Liu, Quan-Zhong
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supporting information
p. 4823 - 4827
(2021/06/28)
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- An expedient route to tricyanovinylindoles and indolylmaleimides fromo-alkynylanilines utilising DMSO as a one-carbon synthon
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A Pd(ii)/Cu(ii) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction proceedsviathe construction of 2-aryl-3-formyl indole followed by sequential addition of malononitrile and a CN resulting
- Chakraborty, Nikita,Dahiya, Anjali,Modi, Anju,Patel, Bhisma K.,Rakshit, Amitava
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p. 6847 - 6857
(2021/08/20)
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- Gold-Catalyzed Cascade and Divergent Synthesis of Indolobenzazepines and Indoloquinolines from Nitrogen-Tethered 1,8-Diynes
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We describe the divergent construction of two nitrogen-containing polycyclic systems by gold-catalyzed cycloisomerizations. The gold-catalyzed cascade hydroamination and 7-endo-dig-selective cycloisomerization of nitrogen-tethered 1,8-diynes yielded indol
- Ito, Mamoru,Onoda, Hideaki,Shibata, Takanori,Takaki, Asahi
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supporting information
(2022/01/22)
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- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
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Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
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supporting information
p. 5599 - 5604
(2021/08/01)
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- A competitive and highly selective 7-, 6- And 5-annulation with 1,3-migration through C-H and N-H-alkyne coupling
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We demonstrated a highly competitive and selective C-C and N-C cross-coupled 7-, 6- and 5-annulation utilizing 2-ethynylanilides to afford functionalized 1H-benzo[b]azepin-2(5H)-ones, 2-quinolinones, and 3-acylindoles in high yield. ZnCl2 was f
- Ajarul, Sk,Kayet, Anirban,Pati, Tanmay K.,Maiti, Dilip K.
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supporting information
p. 474 - 477
(2020/01/13)
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- Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides
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Indole and phthalide are privileged heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1′-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably, only 1.0 mol % of catalyst loading is used, suggesting high efficiency. Late-stage elaborations give highly functionalized analogues.
- Yuan, Shuo,Zhang, Dan-Qing,Zhang, Jing-Ya,Yu, Bin,Liu, Hong-Min
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supporting information
p. 814 - 817
(2020/02/04)
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- Syntheses of N-Alkyl 2-Arylindoles from Saturated Ketones and 2-Arylethynylanilines via Cu-Catalyzed Sequential Dehydrogenation/Aza-Michael Addition/Annulation Cascade
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We describe here a Cu-catalyzed and 4-OH-TEMPO-mediated sequential dehydrogenation/aza-Michael addition/annulation cascade reaction for the construction of N-alkyl 2-arylindoles from facilely available saturated ketones and 2-arylethynylanilines. This rea
- Chen, Linlin,Ling, Fei,Liu, Tao,Ma, Yan,Song, Dingguo,Xiao, Lian,Xu, Min,Yu, Mengyao,Zhong, Weihui
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p. 3224 - 3233
(2020/03/23)
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- Visible-Light-Mediated [2+2+1] Carbocyclization Reactions of 1,7-Enynes with Bromofluoroacetate to Form Fused Monofluorinated Cyclopenta[ c]quinolin-4-ones
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Herein, we describe a new protocol for photoinduced radical [2+2+1] carbocyclization reactions of 1,7-enynes with bromofluoroacetate. These reactions, which proceed via a cascade involving fluoroalkylation, 6-exo-dig and 5-endo-trig cyclizations, H-transf
- Li, Yongqiang,Liu, Yuxiu,Qu, Yi,Song, Hongjian,Wang, Qingmin,Xu, Wentao,Zhang, Jingjing
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p. 5379 - 5389
(2020/05/19)
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- Application of compound containing trifluoromethyl indeno benzo six-membered heterocyclic structure in prevention and treatment of plant diseases and pests
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The invention relates to application of a compound containing a trifluoromethyl indeno benzo six-membered heterocyclic structure in prevention and treatment of plant diseases and pests. The significance of each group in the formula is shown in the specifi
- -
-
Paragraph 0032-0034
(2020/07/02)
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- One-Pot Synthesis of N-Imidoyl-(1 H)-indoles via Palladium-Catalyzed Oxidative Insertion Domino Reaction with Isocyanide and Arylboronic Acid
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Efficient one-pot synthesis of N-imidoyl-(1H)-indoles has been described, which is achieved by the palladium-catalyzed oxidative insertion of 2-(phenylethynyl)aniline, arylboronic acid, and isonitrile. This method provides a new way to synthesize N-imidoy
- Tao, Shou-Wei,Zhou, Jing-Ya,Liu, Rui-Qing,Zhu, Yong-Ming
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p. 8121 - 8130
(2019/06/24)
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- One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
-
An atom-economical method for synthesizing N-heterocyclic indoles from readily available o-alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper-catalyzed cascade bicyclization process consisting of an int
- Xie, Jialin,Guo, Zhonglin,Huang, Yuanqiong,Qu, Yi,Song, Hongjian,Song, Haibin,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 490 - 495
(2019/01/04)
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- On water: iodine-mediated direct construction of 1,3-benzothiazines from ortho-alkynylanilines by regioselective 6-exo-dig cyclization
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Herein, we report the 6-exo-dig ring closure of ortho-alkynylanilines with readily available aroyl isothiocyanate. An environmentally benign, metal- and base-free, iodine promoted cascade synthesis of highly functionalized (benzo[1,3]thiazin-2-yl)benzimid
- Saini, Kapil Mohan,Saunthwal, Rakesh K.,Kumar, Shiv,Verma, Akhilesh K.
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supporting information
p. 2657 - 2662
(2019/03/12)
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- Cobalt-Catalyzed Enantioselective Hydroboration/Cyclization of 1,7-Enynes: Asymmetric Synthesis of Chiral Quinolinones Containing Quaternary Stereogenic Centers
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An asymmetric cobalt-catalyzed hydroboration/cyclization of 1,7-enynes to synthesize chiral six-membered N-heterocyclic compounds was developed. A variety of aniline-tethered 1,7-enynes react with pinacolborane to afford the corresponding chiral boryl-fun
- Wu, Caizhi,Liao, Jiayu,Ge, Shaozhong
-
supporting information
p. 8882 - 8886
(2019/06/13)
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- Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7-Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N-(Acyloxy)phthalimides as Radical Source
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No Abstract. (Figure presented.).
- Correia, José Tiago Menezes,Piva da Silva, Gustavo,André, Elias,Paix?o, Márcio Weber
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supporting information
p. 5558 - 5564
(2019/09/16)
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- Boron Trichloride-Mediated Synthesis of Indoles via the Aminoboration of Alkynes
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We describe an efficient catalyst- and metal-free aminoboration of alkynes to 3-borylated indoles using one of the least expensive boron sources, BCl3. The major dichloro(indolyl)borane products can be used for the in situ construction of usefu
- Lv, Jiahang,Zhao, Binlin,Liu, Li,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
-
supporting information
p. 4054 - 4059
(2018/09/25)
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- Copper-Catalyzed Radical Sulfonylation of N-Propargylindoles with Concomitant 1,2-Aryl Migration
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A novel copper-catalyzed cascade radical sulfonylation of N-propargyl-substituted indoles with concomitant 1,2-aryl migration was described. The protocol, which has good functional-group tolerance, provides practical, versatile and atom-economical method of accessing a new class of fascinating 2-sulfonated pyrrolo[1,2-α]indole derivatives in moderate to good yields through the formation of the new C?S, C?C and C=O bonds in a one-step. (Figure presented.).
- Zhu, Xin-Yu,Han, Ya-Ping,Li, Ming,Li, Xue-Song,Liang, Yong-Min
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supporting information
p. 3460 - 3465
(2018/05/30)
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- Facile Synthesis of π-Conjugated Quinazoline-Substituted Ethenes from 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free Conditions
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A new transition-metal-free version for the synthesis of π-conjugated quinazoline-substituted ethene derivatives from readily available starting materials has been developed. Quinazoline-substituted ethenes were obtained in moderate to high yields with completely Z-selectivity, and the resulting quinazoline-substituted ethenes show typical aggregation-induced emission (AIE) properties.
- Wang, Xu,Li, Jiawei,Huang, Yubing,Zhu, Jiayi,Hu, Rongrong,Wu, Wanqing,Jiang, Huanfeng
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p. 10453 - 10464
(2018/09/06)
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- Palladium-Catalyzed Oxidative [2 + 2 + 1] Annulation of 1,7-Diynes with H2O: Entry to Furo[3,4- c]quinolin-4(5 H)-ones
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A novel cascade annulation of 1,7-diynes with water has been developed for the synthesis of furo[3,4-c]quinolin-4(5H)-one skeletons with high atom- and step-economy. The transformation was enabled by a palladium catalyst in the presence of copper salt as
- Ouyang, Xuan-Hui,Tan, Fang-Lin,Song, Ren-Jie,Deng, Wei,Li, Jin-Heng
-
supporting information
p. 6765 - 6768
(2018/10/24)
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- [3+2]-Annulation of platinum-bound azomethine ylides with distal C=C bonds of N-allenamides
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A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a]indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal C=C bond of N-allenam
- Chakrabarty, Indradweep,Inamdar, Suleman M.,Akram, Manjur O.,Gade, Amol B.,Banerjee, Subhrashis,Bera, Saibal,Patil, Nitin T.
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supporting information
p. 196 - 199
(2016/12/27)
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- Nickel Catalysis Enables Hetero [2+2+1] Cycloaddition between Yne-Isothiocyanates and Isonitriles with Low Catalyst Loading
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Nickel(II) can be used to catalyze the hetero [2+2+1] cycloaddition of 2-alkynylaryl isothiocyanates and isonitriles in 2-methyltetrahydrofuran (2-MeTHF) to give a wide array of thieno[2,3-b]indoles in excellent yields. The reaction is featured by employi
- Liu, Rui-Juan,Wang, Peng-Fei,Yuan, Wen-Kui,Wen, Li-Rong,Li, Ming
-
supporting information
p. 1373 - 1378
(2017/04/18)
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- Rapid Access to Indeno[1,2-c]quinolines via Br?nsted Acid- Catalyzed Cascade Reaction
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A Br?nsted acid-catalyzed annulation strategy has been developed to construct indeno[1,2-c]quinolines. This tandem synthetic method proceeds through a sequential electrophilic addition followed by a Friedel–Crafts-type reaction. A variety of tetracyclic c
- Boominathan, Siva Senthil Kumar,Wang, Jeh-Jeng
-
supporting information
p. 1844 - 1848
(2017/06/09)
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- Copper-catalyzed trifluoromethylazidation and rearrangement of aniline-linked 1,7-enynes: Access to CF3-substituted azaspirocyclic dihydroquinolin-2-ones and furoindolines
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A set of reactions involving copper-catalyzed trifluoromethylazidation and then rearrangement of aniline-linked 1,7-enynes with the relatively poorly reactive Togni reagent I and TMSN3 was developed, and provided facile access to structurally d
- Yu, Liu-Zhu,Wei, Yin,Shi, Min
-
supporting information
p. 8980 - 8983
(2017/08/15)
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- Complex Annulations through Silver Carbenoid Intermediate: An Alternative Entry to Transformations of 1,2,3-Triazoles
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An alternative entry to transformations of N-sulfonyl-4-(2-(ethynyl)aryl)-1,2,3-triazoles with various generated in situ or external nucleophiles by means of silver catalysis for producing diverse functionalized isoquinolines is described. Mechanistically
- Yang, Yuan,Yu, Jiang-Xi,Ouyang, Xuan-Hui,Li, Jin-Heng
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supporting information
p. 3982 - 3985
(2017/08/14)
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- Visible-Light Induced and Oxygen-Promoted Oxidative Cyclization of Aromatic Enamines for the Synthesis of Quinolines Derivatives
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The dual transition metal-visible light photoredox catalysis for the synthesis of quinoline derivatives by using dioxygen as an oxygen source is developed. By using visible light, the direct oxidative cyclization of aromatic enamines with alkynes or alkenes can be achieved at mild conditions with an aid of copper or palladium catalysts, and a variety of multisubstituted quinoline derivatives could be obtained in good to moderate yields under mild reaction conditions.
- Xia, Xiao-Feng,Zhang, Guo-Wei,Wang, Dawei,Zhu, Su-Li
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p. 8455 - 8463
(2017/08/23)
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- A one-pot synthesis of 2,2′-disubstituted diindolylmethanes (DIMs) via a sequential Sonogashira coupling and cycloisomerization/C3-functionalization of 2-iodoanilines
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A Pd(ii)-Ag(i) catalyzed highly efficient synthesis of diindolylmethane has been developed. This transformation consists of a one-pot sequential Sonogashira coupling (and desilylation) followed by cycloisomerization/C3-functionalization of 2-iodoanilines.
- Kayet, Anirban,Singh, Vinod K.
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p. 6997 - 7007
(2017/09/01)
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- Base-Promoted Synthesis of Quinoline-4(1H)-thiones from o-Alkynylanilines and Aroyl Isothiocyanates
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A base-promoted synthesis of quinoline-4(1H)-thiones has been accomplished from the in situ generated o-alkynylthiourea, obtained by reacting o-alkynylanilines with aroyl/acyl isothiocyanates. A 6-exo-dig S-cyclization of the in situ generated thiourea is
- Modi, Anju,Sau, Prasenjit,Patel, Bhisma K.
-
supporting information
p. 6128 - 6131
(2017/11/27)
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- Palladium-Catalyzed Construction of Tetracyclic Scaffolds via the 1,7-Enyne Carbocyclization/Iodophenol Dearomatization Cascade
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An efficient palladium-catalyzed dearomatizing [2+2+1] carbocyclization of 1,7-enynes with iodophenols has been developed. A type of tetracyclic scaffold was built in this reaction, exhibiting a broad substrate scope with moderate to excellent yields. More importantly, this method provides a potential strategy for the synthesis of tetracyclic skeleton natural products.
- Xia, Yu,Wang, Li-Jing,Wang, Jia,Chen, Si,Shen, Yi,Guo, Chun-Huan,Liang, Yong-Min
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p. 12386 - 12394
(2017/12/08)
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- Efficient Modular Synthesis of Substituted Borazaronaphthalene
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A highly efficient modular synthetic method for BN-fused polycyclic aromatic hydrocarbons (PAHs) composed of a borazaronaphthalene core along with multiple functionalized sites is reported. The halogenated 2,1-borazaronaphthalene cores are constructed thr
- Zhuang, Fang-Dong,Han, Ji-Min,Tang, Sheng,Yang, Jing-Hui,Chen, Qi-Ran,Wang, Jie-Yu,Pei, Jian
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supporting information
p. 2479 - 2482
(2017/07/28)
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- Transition-Metal Controlled Diastereodivergent Radical Cyclization/Azidation Cascade of 1,7-Enynes
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A strategy for achieving diastereodivergent azidations of enynes has been developed, employing azide transfer from the M-N3 complex to alkyl radicals. Following this concept, the diastereoselectivity has been switched by modulating the transition metals and the ligands. The Mn(III)-mediated radical cyclization/azidation cascade of 1,7-enynes afforded trans-fused pyrrolo[3,4-c]quinolinones, whereas the Cu(II)/bipyridine system gave cis-products.
- Zhao, Yingying,Hu, Yancheng,Wang, Haolong,Li, Xincheng,Wan, Boshun
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p. 4412 - 4420
(2016/06/09)
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- Access to Indole Derivatives from Diaryliodonium Salts and 2-Alkynylanilines
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An efficient, environmentally friendly, and operationally simple procedure to 1,2-disubstituted indoles from 2-alkynylanilines and diaryliodonium salts has been developed. This reaction proceeds smoothly under metal-free conditions. The products obtained could be transferred into 3,3′-diindolylmethane with DMSO catalyzed by palladium. The isotopic label experiments indicated that the methylene group in 3,3′-diindolylmethane is derived from DMSO. The diverse indoles were obtained in up to 90% yield for 28 examples.
- Li, Pengfei,Weng, Yunxiang,Xu, Xianxiang,Cui, Xiuling
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p. 3994 - 4001
(2016/06/09)
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- Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
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Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a
- Youn, So Won,Lee, So Ra
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p. 4652 - 4656
(2015/04/27)
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- Expedient Access to Unsymmetrical Diarylindolylmethanes through Palladium-Catalyzed Domino Electrophilic Cyclization-Extended Conjugate Addition Approach
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A palladium-catalyzed domino process to access unsymmetrical diarylindolylmethanes has been developed through the annulation of o-alkynylanilines followed by 1,6-conjugate addition with p-quinone methides (p-QMs) under relatively mild conditions. The broad substrate scope of this methodology was demonstrated through the use of a wide range of substituted o-alkynylanilines and p-quinone methides, and in most cases, the unsymmetrical diarylindolylmethanes could be prepared in moderate to excellent yields. Notably, this method does not require any amino group protection. Moreover, 100% atom economy makes this transformation attractive from a green chemistry perspective.
- Reddy, Virsinha,Vijaya Anand, Ramasamy
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supporting information
p. 3390 - 3393
(2015/07/28)
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- P-TsOH Promoted Au(I)-Catalyzed Consecutive Endo Cyclization of Yne-Tethered Ynamide: Access to Benzofused Dihydroisoquinolones
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A novel synthetic route to benzo[f]dihydroisoquinolone through a p-TsOH promoted cascade cyclization of easily accessible diyne-tethered ynamides in the presence of a Au(I)-catalyst is described. This reaction unveils a broad substrate scope, constructing a wide range of benzo[f]dihydroisoquinolones in good yields. The diyne-tethered ynamides are synthesized from inexpensive o-iodoaniline through Sonogashira couplings and the Cu-mediated C-N bond formation. The role of p-TsOH is examined, and the reaction pathway is also deduced. The benzo[f]isoquinoline scaffold is constructed from benzo[f]dihydroisoquinolones.
- Nayak, Sanatan,Ghosh, Nayan,Prabagar,Sahoo, Akhila K.
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supporting information
p. 5662 - 5665
(2015/12/01)
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- TBHP mediated oxidation of N-2-alkynylphenyl α-amino carbonyl compounds to oxalic amides using visible light photoredox catalysis and their application in the synthesis of 2-aryl indoles
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A visible light promoted and TBHP mediated oxidative reaction of N-2-alkynylphenyl α-amino carbonyl compounds to N-2-alkynylphenyl oxalic amides was developed. In the presence of CuBr and photocatalyst Ru(bpy)3Cl2·6H2O, the reaction proceeded smoothly to afford the corresponding oxalic amides under the irradiation of a 26 W compact fluorescence bulb at room temperature. Furthermore, N-2-alkynylphenyl oxalic amides could be subsequently transferred to 2-aryl indoles without an additional deacylation step through a favored 5-endo-dig N-cyclization process using AgNO3 as catalyst.
- Liu, Wei,Liu, Sheng,Xie, Hongqi,Qing, Zhixing,Zeng, Jianguo,Cheng, Pi
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p. 17383 - 17388
(2015/03/04)
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- ZnBr2-mediated synthesis of indoles in a ball mill by intramolecular hydroamination of 2-alkynylanilines
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A method for the intermolecular hydroamination of 2-alkynylanilines in a planetary ball mill is described, which avoids the use of solvents during the reaction. Different additives were tested, whereby ZnBr2 in stoichiometric amounts showed the best performance in terms of yield and selectivity. Furthermore, the materials used for milling balls and beakers as well as the milling time and the rotation frequency were changed in order to achieve the best reaction conditions. As a result, two methods for the synthesis of 2-substituted 1H-indoles are described with their respective advantages and disadvantages. Both methods were used to convert different alkyl and aryl containing 2-ethynylanilines. This journal is the Partner Organisations 2014.
- Zille, Markus,Stolle, Achim,Wild, Andreas,Schubert, Ulrich S.
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p. 13126 - 13133
(2014/04/03)
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- Silver-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines: Highly efficient synthesis of structurally diverse fluorinated indole derivatives
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Highly efficient approaches to obtain structurally diverse fluorinated indole derivatives have been realized through the Ag-catalyzed one-pot cyclization/fluorination of 2-alkynylanilines in the presence of NFSI or Selectfluor. The Royal Society of Chemistry.
- Yang, Lei,Ma, Yuanhong,Song, Feijie,You, Jingsong
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supporting information
p. 3024 - 3026
(2014/03/21)
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- A robust, well-defined homogeneous silver(I) catalyst for mild intramolecular hydroamination of 2-ethynylanilines leading to indoles
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A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives. Copyright
- McNulty, James,Keskar, Kunal
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p. 1622 - 1629
(2014/03/21)
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- A Robust, Well-Defined Homogeneous Silver(I) Catalyst for Mild Intramolecular Hydroamination of 2-Ethynylanilines Leading to Indoles
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A highly efficient, chemically stable and well-defined homogeneous silver(I) catalyst is reported for the room temperature, intramolecular hydroamination of 2-alkynylanilines leading to indole derivatives.
- McNulty, James,Keskar, Kunal
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p. 1622 - 1629
(2015/10/05)
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- Synthesis of bis-exocyclic conjugated diene containing 1,2,3,4-tetrahydroquinoline derivatives via palladium-catalyzed intramolecular Heck cyclization
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An efficient method has been developed for the synthesis of bis-exocyclic conjugated diene containing 1,2,3,4-tetrahydroquinoline derivatives via palladium-catalyzed intramolecular Heck cyclization of (2-bromo-allyl)-(2-phenylethynyl-phenyl)-amines. The r
- Ghosh, Munmun,Dhara, Shubhendu,Nuree, Yasin,Ray, Jayanta K.
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p. 41561 - 41564
(2014/12/10)
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- Synthesis of bis-exocyclic conjugated diene containing 1,2,3,4-tetrahydroquinoline derivatives via palladium-catalyzed intramolecular Heck cyclization
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An efficient method has been developed for the synthesis of bis-exocyclic conjugated diene containing 1,2,3,4-tetrahydroquinoline derivatives via palladium-catalyzed intramolecular Heck cyclization of (2-bromo-allyl)-(2-phenylethynyl-phenyl)-amines. The r
- Ghosh, Munmun,Dhara, Shubhendu,Nuree, Yasin,Ray, Jayanta K.
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p. 41561 - 41564
(2015/05/20)
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- Diaceno[a,e]pentalenes from homoannulations of o-alkynylaryliodides utilizing a unique Pd(OAc)2/n-Bu4NOAc catalytic combination
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A heterogeneous catalytic system, Pd(OAc)2/n-Bu4NOAc, for the efficient synthesis of diaceno[a,e]pentalenes via a tandem Pd catalytic cycle is reported. The catalytic partner n-Bu4NOAc played indispensable and versatile ro
- Shen, Junjian,Yuan, Dafei,Qiao, Yan,Shen, Xingxing,Zhang, Zhongbo,Zhong, Yuwu,Yi, Yuanping,Zhu, Xiaozhang
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supporting information
p. 4924 - 4927
(2015/04/27)
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- Cycloisomerization of 2-alkynylanilines to indoles catalyzed by carbon-supported gold nanoparticles and subsequent homocoupling to 3,3′-biindoles
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Elevated by the support: 2-Alkynyl aniline cycloisomerization to indole is catalyzed by cationic Au NPs on a carbon support. Electroneutral and rich 2-aryl indoles are further converted into 3,3′-biindoles by oxidative homocoupling that is readily catalyzed by the Au NPs on carbon, and exclusively but also somewhat sluggishly by the carbon support. Copyright
- Perea-Buceta, Jesus E.,Wirtanen, Tom,Laukkanen, Otto-Ville,Maekelae, Mikko K.,Nieger, Martin,Melchionna, Michele,Huittinen, Nina,Lopez-Sanchez, Jose A.,Helaja, Juho
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supporting information
p. 11835 - 11839
(2013/11/19)
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- Protonated DBU as catalyst for cascade addition-cyclization of 2-alkynylaniline and carbon disulfide
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Protonated 1,8-diazabicyclo[5,4,0]undec-7-ene as catalyst for cascade addition/cyclization of 2-alkynylaniline and carbon disulfide has been described. This process provides a convenient route for synthesis of a variety of benzo[d][1,3]thiazine-2(4H)-thio
- Zhao, Peng,Liao, Qian,Gao, Hongxin,Xi, Chanjuan
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supporting information
p. 2357 - 2361
(2013/06/26)
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- A practical protocol for three-component, one-pot, stepwise sonogashira-heterocyclization-heck couplings
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A three-component, one-pot, stepwise Sonogashira-heterocyclization-Heck- coupling process was developed starting from either haloarenecarboxamides, halophenols or haloanilines, terminal alkynes and electron-deficient alkenes. Cyclic imidate-, benzofuran-,
- Madich, Youssef,Denis, J.Gabriel,Ortega, Aitor,Martinez, Claudio,Matrane, Abdellatif,Belachemi, Larbi,De Lera, Angel R.,Alvarez, Rosana,Aurrecoechea, Jose M.
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p. 2009 - 2017
(2013/07/26)
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