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Belenkii et al.
(1971)
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Trinuclear ruthenium carbonyl complexes with salicylaldimine ligands as efficient catalysts for the oxidation of secondary alcohols
A series of novel trinuclear ruthenium carbonyl complexes [μ-?2-2-OC6H4-CH=N-Ar)]2Ru3(CO)8 [Ar = Ph (8), C6H4-4-Me (9), C6H4-4-CF3 (10), C6H4-4-Cl (11), C6H3-2,6-Me2 (12), C6H3-2,6-Et2 (13)] and [μ-?2-2-OC6H4-CH=N-C6H3-2,6-iPr2]Ru3(CO)9 (14) were designed and synthesized. All the seven novel complexes were fully characterized by elemental analysis, IR and NMR spectroscopy. Molecular structures of 8, 11, 13 and 14 were further confirmed by single-crystal X-ray diffraction. The catalytic performance of these complexes in the oxidation of secondary alcohols was explored and it was found the combination of such complexes and N-methylmorpholine-N-oxide (NMO) exhibits high catalytic activities for the oxidation of secondary alcohols, giving the corresponding carbonyl compounds in excellent yields.
Han, Zhangang,Hao, Zhiqiang,Li, Ying,Lin, Jin,Lu, Guo-Liang,Ma, Zhihong
(2021)
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Efficient aerobic oxidation of alcohols to aldehydes and ketones using a ruthenium carbonyl complex of a tert-butyl-substituted tetramethylcyclopentadienyl ligand as catalyst
Tert-butyl-substituted tetramethylcyclopentadiene [C5HMe4tBu] was reacted with Ru3(CO)12 to prepare [(η5-C5Me4tBu)Ru(CO)(μ-CO)]2. The complex was characterized by IR, 1H NMR, 13C NMR, elemental analysis, and single-crystal X-ray diffraction. The complex was investigated as a catalyst in the aerobic oxidation of alcohols to the corresponding aldehydes and ketones in the presence of 2,2’,6,6’-tetramethylpiperidine N-oxide (TEMPO) as co-oxidant. The combination of [(η5-C5Me4tBu)Ru(CO)(μ-CO)]2 and TEMPO afforded an efficient catalytic system for the aerobic oxidation of a variety of primary and secondary alcohols, giving the corresponding carbonyl compounds in good-to-excellent yields.
Hao, Zhiqiang,Yan, Xinlong,Li, Zhanwei,Wu, Ruitao,Ma, Zhihong,Li, Suzhen,Han, Zhangang,Zheng, Xuezhong,Lin, Jin
p. 635 - 640
(2018)
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Ruthenium carbonyl complexes supported by pyridine-alkoxide ligands: Synthesis, structure and catalytic oxidation of secondary alcohols
Five novel trinuclear ruthenium complexes [[PyCHC(RC6H4)O]2Ru3(CO)8] [R = 4-OMe (6), 4-Br (7), 4-CF3 (8)] and [[PyCH2CH(RC6H4)O]2Ru3(CO)8] [R = 2-Br (9), 2-CF3 (10)], were synthesized by treating Ru3(CO)12 with two equivalents of the corresponding pyridine-alcohols PyCH2CH(RC6H4)OH [1-5, R = 4-OMe, 4-Br, 4-CF3, 2-Br and 2-CF3] in refluxing toluene. The structures of 6-10 were fully characterized by IR and NMR spectroscopy, elemental analysis and single-crystal X-ray diffraction. They were found to be efficient catalysts for the oxidation of secondary alcohols by NMO, giving the corresponding ketones in good to excellent yields within 15 min, of which [PyCHC(4-OCH3C6H4)O]2Ru3(CO)8 (6) is the best.
Zong, Siqi,Liu, Kang,Yue, Xiaohui,Hao, Zhiqiang,Ma, Zhihong,Han, Zhangang,Lu, Guo-Liang,Lin, Jin
p. 13947 - 13953
(2019)
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Stepwise benzylic oxygenation via uranyl-photocatalysis
Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.
Hu, Deqing,Jiang, Xuefeng
supporting information
p. 124 - 129
(2022/01/19)

Visible light-mediated, high-efficiency oxidation of benzyl to acetophenone catalyzed by fluorescein
An environmentally friendly aerobic oxidation of benzyl C(sp3)-H bonds to ketones via selective oxidation catalysis was developed. Fluorescein is an efficient photocatalyst with excellent chemical selectivity. The reaction has a wide substrate scope, and a successful gram-scale experiment demonstrated its potential industrial utility.
Geng, Haoxing,Liu, Xin,Zhu, Qing
supporting information

(2021/12/20)

Ruthenium(II) Complexes Bearing Schiff Base Ligands for Efficient Acceptorless Dehydrogenation of Secondary Alcohols?
Four ruthenium(II) complexes 1—4 [RN=CH-(2,4-(tBu)2C6H2O)]RuH(PPh3)2(CO) (R = C6H5, 1; R = 4-MeC6H4, 2; R = 4-ClC6H4, 3; R = 4-BrC6H4, 4) bearing Schiff base ligands were prepared by treating RuHClCO(PPh3)3 with RN=CH-(2,4-(tBu)2C6H2OH (L1—L4) in the presence of triethylamine. Their structures were fully characterized by elemental analysis, IR, NMR spectroscopy and X-ray crystallography. These Ru(II) complexes exhibit high catalytic performance and good functional-group compatibility in the acceptorless dehydrogenation of secondary alcohols, affording the corresponding ketones in 82%—94% yields.
Dong, Qing,Feng, Qi,Han, Zhangang,Hao, Zhiqiang,Lin, Jin,Liu, Kang,Lu, Guo-Liang,Ma, Dongzhu
p. 121 - 128
(2020/12/25)

Preparation of trinuclear ruthenium clusters based on piconol ligands and their application in Oppenauer-type oxidation of secondary alcohols
Treatment of Ru3(CO)12 with one equivalent of 2-indolyl-6-pyridinyl-alcohol ligands 2-(C8H6N)-6-(CR1R2OH)C5H3N (R1 = R2 = Me (L1H); R1 = R2 = C2H5 (L2H); R1, R2 = ?(CH2)4- (L3H);& R1, R2 = ?(CH2)5- (L4H)) in refluxing THF afforded the corresponding trinuclear ruthenium clusters L(μ2-H)Ru3(CO)9 (1a–1d), respectively. All the novel Ru complexes were well characterized by NMR, elemental analyses and IR spectra. Structures of complexes 1a, 1c, and 1d were further determined by X-ray crystallographic studies. Complexes 1a–1d were applied to catalytic Oppenauer-type oxidation of secondary alcohols with acetone as oxidant, and complex 1a was found to be the most efficient catalyst.
Dong, Qing,Ma, Zongwen,Hao, Zhiqiang,Han, Zhangang,Lin, Jin,Lu, Guo-Liang
(2021/06/18)

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions
A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.
Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu
p. 12344 - 12353
(2021/09/02)

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information
p. 5905 - 5908
(2021/06/18)

Site-Specific Oxidation of (sp3)C-C(sp3)/H Bonds by NaNO2/HCl
A site-specific oxidation of (sp3)C-C(sp3) and (sp3)C-H bonds in aryl alkanes by the use of NaNO2/HCl was explored. The method is chemical-oxidant-free, transition-metal-free, uses water as the solvent, and proceeds under mild conditions, making it valuable and attractive to synthetic organic chemistry.
Zhao, Jianyou,Shen, Tong,Sun, Zhihui,Wang, Nengyong,Yang, Le,Wu, Jintao,You, Huichao,Liu, Zhong-Quan
p. 4057 - 4061
(2021/05/26)

Hydration of Alkynes to Ketones with an Efficient and Practical Polyoxomolybdate-based Cobalt Catalyst
Hydration of alkynes to ketones is one of the most atom economical and universal methods for the synthesis of carbonyl compounds. However, the basic reaction usually requires organic ligand catalysts or harsh reaction conditions to insert oxygen into the C≡C bond. Here, we report an inorganic ligand supported cobalt (III) catalyst, (NH4)3[CoMo6O18(OH)6], which is supported by a central cobalt (III) mononucleus and a ring-shaped pure inorganic ligand composed of six MoVIO6 octahedrons to avoid the disadvantages of expensive and unrecyclable organic ligand catalysts or noble metal catalysts. Under mild conditions, the cobalt (III) catalyst can be used for the hydration of alkynes to ketones. The catalyst is non-toxic, green, and environment friendly. The catalyst can be recycled at least six times with high activity. According to control experiments, a reasonable mechanism is provided.
Xie, Ya,Wang, Jingjing,Wang, Yunyun,Han, Sheng,Yu, Han
p. 4985 - 4989
(2021/10/12)

Dual-Metal N-Heterocyclic Carbene Complex (M = Au and Pd)-Functionalized UiO-67 MOF for Alkyne Hydration-Suzuki Coupling Tandem Reaction
Metal N-heterocyclic carbene complexes (NHC-M) have been recognized as an important class of organometallic catalysts. Herein, we demonstrate that different NHC-M (M = Au and Pd) species can be simultaneously introduced into a single metal organic framework (MOF) by direct assembly of NHC-M-decorated ligands and metal ions under solvothermal conditions. The obtained UiO-67-Au/Pd-NHBC MOF with different organometallic NHC-M species can be a highly reusable dual catalyst to sequentially promote alkyne hydration-Suzuki coupling reaction. The potential utility of this strategy is highlighted by the preparation of many more new multicatalysts of this type for various organic transformations in a sequential way.
Dong, Ying,Li, Wen-Han,Dong, Yu-Bin
p. 1818 - 1826
(2021/01/13)

Chitosan as a chiral ligand and organocatalyst: Preparation conditions-property-catalytic performance relationships
Chitosan is an abundant and renewable chirality source of natural origin. The effect of the preparation conditions by alkaline hydrolysis of chitin on the properties of chitosan was studied. The materials obtained were used as ligands in the ruthenium-catalysed asymmetric transfer hydrogenation of aromatic prochiral ketones and oxidative kinetic resolution of benzylic alcohols as well as organocatalysts in the Michael addition of isobutyraldehyde to N-substituted maleimides. The degrees of deacetylation of the prepared materials were determined by 1H NMR, FT-IR and UV-vis spectroscopy, the molecular weights by viscosity measurements, their crystallinity by WAXRD, and their morphology by SEM and TEM investigations. The materials were also characterized by Raman spectroscopy. The biopolymers which have molecular weights in a narrow (200-230 kDa) range and appropriate (80-95%) degrees of deacetylation were the most efficient ligands in the enantioselective transfer hydrogenation, whereas in the oxidative kinetic resolution the activity of the complexes and the stereoselectivity increased with the degree of deacetylation. The chirality of the chitosan was sufficient to obtain enantioselection in the Michael addition of isobutyraldehyde to maleimides in the aqueous phase. Interestingly, the biopolymer afforded the opposite enantiomer in excess compared to the monomer, d-glucosamine. In this reaction, good correlation between the degree of deacetylation and the catalytic activity was found. These results are novel steps in the application of this natural, biocompatible and biodegradable polymer in developing environmentally benign methods for the production of optically pure fine chemicals.
Kolcsár, Vanessza Judit,Sz?ll?si, Gy?rgy
p. 7652 - 7666
(2021/12/13)

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride
Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.
Duan, Limei,Li, Peihe,Li, Wanfei,Liu, Jinghai,Liu, Ying,Liu, Zhifei,Lu, Ye,Sarina, Sarina,Wang, Jinghui,Wang, Yin,Wang, Yingying,Zhu, Huaiyong
p. 4429 - 4438
(2021/07/12)

Flexible on-site halogenation paired with hydrogenation using halide electrolysis
Direct electrochemical halogenation has appeared as an appealing approach in synthesizing organic halides in which inexpensive inorganic halide sources are employed and electrical power is the sole driving force. However, the intrinsic characteristics of direct electrochemical halogenation limit its reaction scope. Herein, we report an on-site halogenation strategy utilizing halogen gas produced from halide electrolysis while the halogenation reaction takes place in a reactor spatially isolated from the electrochemical cell. Such a flexible approach is able to successfully halogenate substrates bearing oxidatively labile functionalities, which are challenging for direct electrochemical halogenation. In addition, low-polar organic solvents, redox-active metal catalysts, and variable temperature conditions, inconvenient for direct electrochemical reactions, could be readily employed for our on-site halogenation. Hence, a wide range of substrates including arenes, heteroarenes, alkenes, alkynes, and ketones all exhibit excellent halogenation yields. Moreover, the simultaneously generated H2at the cathode during halide electrolysis can also be utilized for on-site hydrogenation. Such a strategy of paired halogenation/hydrogenation maximizes the atom economy and energy efficiency of halide electrolysis. Taking advantage of the on-site production of halogen and H2gases using portable halide electrolysis but not being suffered from electrolyte separation and restricted reaction conditions, our approach of flexible halogenation coupled with hydrogenation enables green and scalable synthesis of organic halides and value-added products.
Shang, Xiao,Liu, Xuan,Sun, Yujie
supporting information
p. 2037 - 2043
(2021/03/26)

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for aerobic oxidation of alcohols
A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidation of alcohols has been developed for the first time, and the photoredox aerobic oxidation of secondary and primary alcohols provided the corresponding ketones and carboxylic acids, respectively, in high to excellent yields.
Zhu, Xianjin,Liu, Can,Liu, Yong,Yang, Haijun,Fu, Hua
p. 12443 - 12446
(2020/10/30)

Highly efficient oxidation of alcohols catalyzed by Ru(II) carbonyl complexes bearing salicylaldiminato ligands
Reaction of Ru3(CO)12 with 2.0 equiv of RN = CH(3,5-tBu2C6H2OH) (R = C6H5, L1; R = 4-MeC6H4, L2; R = 4-OMeC6H4, L3; R = 4-ClC6H4, L4; R = 4-BrC6H4, L5; R = 4-CF3C6H4, L6) in refluxing xylene afforded the corresponding bis-chelate Ru(II) complexes 1a–1f [RN = CH(3,5-tBu2C6H2O)]2Ru(CO)2 and one of the imine bonds reduced complexes {[RN = CH(3,5-tBu2C6H2O)]-[RNH-CH2(3,5-tBu2C6H2O)]}Ru(CO)2 2a–2f. All the ruthenium complexes were fully characterized by NMR, IR and elemental analysis. In addition, the structures of complexes 1a–1f, 2b, 2d and 2f were further confirmed by single-crystal X-ray diffraction. When activated with N-methylmorpholine-N-oxide (NMO), these Ru complexes displayed high catalytic activities toward oxidation of both 1° and 2° alcohols. For most cases, the reaction can complete within 1 h in refluxing CH3CN.
Dong, Qing,Han, Zhangang,Hao, Zhiqiang,Huo, Shuaicong,Lin, Jin,Liu, Kang,Lu, Guo-Liang,Zhang, Junhua
(2019/11/03)

Manganese/Copper Co-catalyzed Electrochemical Wacker-Tsuji-Type Oxidation of Aryl-Substituted Alkenes
A manganese/copper co-catalyzed electrochemical Wacker-Tsuji-type oxidation of aryl-substituted alkenes has been developed. The process involves the use of 5 mol % MnBr2 and 7.5 mol % CuCl2, in 4:1 acetonitrile/water in an undivided cell at 60 °C, with 2.8 V constant applied potential. α-Aryl ketones are formed in moderate to excellent yields, with the advantages of avoidance of palladium as a catalyst and any external chemical oxidant in an easily operated, cost-effective procedure.
Lai, Junshan,Pericàs, Miquel A.
supporting information
p. 7338 - 7342
(2020/10/02)

Isopropanol as a hydrogen source for single atom cobalt-catalyzed Wacker-type oxidation
The first example of a heterogeneous cobalt catalytic system for Wacker-type oxidation catalyzed by a single atom dispersed Co-N/C catalyst using alcohol as the hydrogen source under an oxygen atmosphere is presented. By combining a well-designed, controlled experiment and various methods of characterization, we determined that single atom cobalt was the active center rather than nanoparticle or oxide counterparts.
An, Yue,Chen, Bo,Gao, Shuang,Huang, Guanwang,Luo, Huihui,Shang, Sensen,Wang, Lianyue
p. 2769 - 2773
(2020/06/17)

Selective Oxidation of Benzylic C-H Bonds Catalyzed by Cu(II)/{PMo12}
Precise catalytic regulation of carbon radical generation by a highly active oxygen radical to abstract the H atom in a C-H bond is an effective method for the selective activation of C-H synthetic chemistry. Herein, we report a facile catalyst system with commercially available copper(II)/{PMo12} to form a tert-butanol radical intermediate for the selective oxidation of benzylic C-H bonds. The reaction shows a broad range of substrates (benzyl methylene, benzyl alcohols) with good functional group tolerance and chemical selectivity. The corresponding carbonyl compounds were synthesized with good yields under mild conditions. DFT calculations and experimental analysis further demonstrated a reasonable carbon radical mechanism for this type of organic transformation reaction.
Li, Peihe,Wang, Yingying,Wang, Xia,Wang, Yin,Liu, Ying,Huang, Keke,Hu, Jing,Duan, Limei,Hu, Changwen,Liu, Jinghai
p. 3101 - 3109
(2020/03/23)

Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
supporting information
p. 4357 - 4363
(2020/07/14)

Half-sandwich ruthenium-based versatile catalyst for both alcohol oxidation and catalytic hydrogenation of carbonyl compounds in aqueous media
A series of half-sandwich ruthenium-based catalysts for both alcohol oxidation and carbonyl compounds hydrogenation have been synthesized through metal-induced C–H bond activation based on benzothiazole ligands. The neutral ruthenium complexes 1–4 were fully characterized by UV–vis, NMR, IR, and elemental analysis. Molecular structures of complexes 1 and 3 were further confirmed by X-ray diffraction analysis. All complexes exhibited high activity for the catalytic oxidation of a variety of alcohols with tBuOOH as oxidants to give carbonyl compounds with high yields in water. Moreover, these half-sandwich complexes also showed high efficiency for the catalytic hydrogenation of carbonyl compounds in a methanol–water mixture. The catalyst could be reused for at least five cycles without any loss of activity. The catalytic system also worked well for various kinds of substrates with either electron-donating or electron-withdrawing groups.
Qiao, Xin-Chao,Qiu, Dan-Chen,Lin, Nan,Zhu, Jing-Wei,Deng, Wei,Yao, Zi-Jian
(2019/03/17)

Efficient Palladium(0) supported on reduced graphene oxide for selective oxidation of olefins using graphene oxide as a ‘solid weak acid’
Selective oxidation of olefin derivatives to ketones has made innovative development over palladium(0) supported on reduced graphene oxide. Compared to traditional Wacker oxidation, the novel method offers an economical and environment-friendly option by using graphene oxide (GO) as a ‘solid weak acid’ instead of classical homogeneous catalysts like H2SO4 and CF3COOH. X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscope and transmission electron microscopy images of Pd0/RGO showed that the nanoscaled Pd particles generated at the flake structure of reduced graphene oxide. Under optimized condition, up to 44 kinds of ketones with different structures can be prepared with excellent yields.
Gao, Xi,Zhou, Jianhao,Peng, Xinhua
p. 73 - 78
(2019/02/06)

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations
Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.
Betori, Rick C.,May, Catherine M.,Scheidt, Karl A.
p. 16490 - 16494
(2019/11/03)

Synthesis method of primary amine hydrochloride
The invention discloses a synthesis method of primary amine hydrochloride. According to the synthesis method, in the presence of a gold complex, water and alkyne carry out catalytic hydrolysis to generate ketones, and then ketones and ammonium formate are catalyzed by a rhodium complex to generate primary amine. Compared with a conventional primary amine synthesis method, the synthesis method hasthe advantages that no alkali is added during the reaction process, no side product is generated, the atomic economy is good, the reaction conditions are mild, and the synthesis method has a wide prospect.
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Paragraph 0109-0112

(2019/03/09)

Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions
An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramolecular species (FeMo6·2Br), which can effectively catalyze the reaction.
Yu, Han,Zhao, Qixin,Wei, Zheyu,Wu, Zhikang,Li, Qi,Han, Sheng,Wei, Yongge
supporting information
p. 7840 - 7843
(2019/07/12)

Synthesis method for aromatic ring bromination of acetophenones derivative
The invention relates to a synthesis method for aromatic ring bromination of an acetophenones derivative, and belongs to the technical field of organic synthesis. The synthesis method consists of twokinds of synthesis methods: method A, adding the acetophenone derivative into a first oxidizing agent and stirring to form a suspension system, controlling the temperature of the suspension system tobe 10-50 DEG C, adding a first reducing agent or a second reducing agent, stirring and reacting for 2-20 h, and performing aftertreatment after the reaction is completed to obtain the aromatic ring brominated acetophenone derivative; method B, adding the acetophenone derivative into the second reducing agent and stirring to form a suspension system, controlling the temperature of the suspension system to be 10-50 DEG C, then adding a second oxidizing agent or the first oxidizing agent, stirring and reacting for 2-20 h, and performing aftertreatment after the reaction is completed to obtain thearomatic ring brominated acetophenone derivative. According to the synthesis method provided by the invention, an inorganic and non-toxic bromination reagent is used, water is used as a reaction solvent, the prepared product is mutually incompatible with water, so that separation and the aftertreatment are convenient to perform, therefore, the synthesis method of the invention is applicable to large-scale industrial production of intermediate products for aromatic ring bromination of the acetophenones derivative.
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Paragraph 0075-0078

(2019/06/11)

Pyridinemethanol-containing ruthenium carbonyl complex and application thereof
The invention discloses a pyridinemethanol-containing ruthenium carbonyl complex and application thereof. A structural expression formula of the pyridinemethanol-containing ruthenium carbonyl complexis shown as follows: a formula is shown in the description; the application is that the pyridinemethanol-containing ruthenium carbonyl complex is used as a catalyst and is used for catalyzing an alcohol type compound to be subjected to dehydrogenation oxidization reaction in the presence of alkali, so as to synthesize aldehyde and ketone derivatives. Synthesis steps of the pyridinemethanol-containing ruthenium carbonyl complex disclosed by the invention are simple and convenient. The range of a catalysis substrate is wide and the complex has relatively good tolerance on various functional groups; a few of byproducts are generated and the complex has the advantages of good thermal stability, high catalytic activity, short reaction time and small catalyst dosage in catalytic reaction.
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Paragraph 0062; 0063; 0065; 0066

(2018/12/02)

Preparation method of aromatic ketone
The invention discloses a preparation method of aromatic ketone. Under the effects of a palladium catalyst and a nitrogen-containing ligand, nitrile compounds and arylsulfonylhydrazide take desulfurization addition reaction in an organic solvent; after the reaction is completed, post treatment is performed to obtain aromatic ketone. The reaction is applicable to aromatic nitrile compounds, and isalso applicable to aliphatic nitrile compounds; the reaction realizes the wide substrate applicability and functional group tolerance; the potential application value is realized in the aspect of aryl-carbonyl building.
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Paragraph 0056; 0057; 0058; 0060

(2018/09/11)

Ruthenium carbonyl complexes with pyridylalkanol ligands: Synthesis, characterization and catalytic properties for aerobic oxidation of secondary alcohols
Reaction of Ru3(CO)12 with pyridylalkanol ligands PyC(CH2)4OH (L1H), PyC(CH2)5OH (L2H) and PyCR1R2OH (R1 = R2 = CH3 (L3H); R1 = CH3, R2 = C6H5 (L4H); R1 = H, R2 = C6H5 (L5H); R1 = H, R2 = 4-CH3C6H4 (L6H); R1 = H, R2 = 4-OMeC6H4 (L7H); R1 = H, R2 = 4-ClC6H4 (L8H); R1 = H, R2 = 4-BrC6H4 (L9H); R1 = H, R2 = 4-CF3C6H4 (L10H)) in refluxing xylene afforded the bis-chelate ruthenium carbonyl complexes [(Ln)2Ru3(CO)8] (n = 1 (1a); n = 2 (1b); n = 3 (1c); n = 4 (1d); n = 5 (1e); n = 6 (1f); n = 7 (1g); n = 8 (1h); n = 9 (1i); n = 10 (1j)), respectively. All the novel ruthenium complexes were fully characterized by NMR, elemental analyses and IR spectra and the molecular structures of 1a, 1c, 1e, 1g and 1i were further determined by single crystal X-ray diffraction analysis. In the presence of TEMPO (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxyl), these trirhenium carbonyl clusters displayed high reactivity for aerobic oxidation of secondary alcohols to give the corresponding ketonic compounds in good to excellent yield using ambient air as the source of oxidant.
Hao, Zhiqiang,Li, Ning,Yan, Xinlong,Li, Ying,Zong, Siqi,Liu, Huating,Han, Zhangang,Lin, Jin
p. 6968 - 6975
(2018/05/04)

Ruthenium carbonyl complexes with pyridine-alkoxide ligands: Synthesis, characterization and catalytic application in dehydrogenative oxidation of alcohols
Several new trinuclear ruthenium carbonyl complexes chelated with 6-bromopyridine alcohol ligands, [6-bromopyC(CH2)4O]Ru3(CO)9 (1a), [6-bromopyC(CH2)5O]Ru3(CO)9 (1b), [6-bromopyC(Me)2O]Ru3(CO)9 (1c) and [6-bromopyCMeC6H5O]Ru3(CO)9 (1d), were synthesized by the reaction of Ru3(CO)12 with 6-bromopyC(CH2)4OH (L1H), 6-bromopyC(CH2)5OH (L2H), 6-bromopyC(Me)2OH (L3H) and 6-bromopyCMeC6H5OH (L4H) in refluxing THF, respectively. The free ligands L1H-L4H were synthesized by the nucleophilic reaction of lithium salt (generated from 2,6-dibromopyridine and n-BuLi) with the corresponding ketones. Furthermore, these pyridine-based ligands were characterized by NMR spectroscopy and elemental analyses. All the four ruthenium carbonyl complexes were well characterized by NMR, IR, single-crystal X-ray crystallography, etc. Complexes 1a-1d were found to exhibit high catalytic activities for the dehydrogenative oxidation of secondary alcohols to give their corresponding products in good to excellent yields.
Hao, Zhiqiang,Yan, Xinlong,Liu, Kang,Yue, Xiaohui,Han, Zhangang,Lin, Jin
p. 15472 - 15478
(2018/09/29)

Synthesis, characterization and catalytic activities of rhenium carbonyl complexes bearing pyridine-alkoxide ligands
Thermal treatment of Re2(CO)10 with pyridine-alkoxide ligands PyC(CH2)4OH (LaH) and PyCR1R2OH (R1 = CH3, R2 = C6H5 (LbH); R1 = H, R2 = C6H5 (LcH); R1 = H, R2 = 4-CH3C6H4 (LdH); R1 = H, R2 = 4-OMeC6H4 (LeH); R1 = H, R2 = 4-ClC6H4 (LfH); R1 = H, R2 = 4-CF3C6H4 (LgH)) respectively in refluxing xylene generated a series of dirhenium carbonyl complexes [PyC(CH2)4O]2 [Re(CO)3]2 (1a) and (PyCR1R2O)2 [Re(CO)3]2 (R1 = CH3, R2 = C6H5 (1b); R1 = H, R2 = C6H5 (1c); R1 = H, R2 = 4-CH3C6H4 (1d); R1 = H, R2 = 4-OMeC6H4 (1e); R1 = H, R2 = 4-ClC6H4 (1f); R1 = H, R2 = 4-CF3C6H4 (1g)). Complexes 1a?1g were characterized by NMR spectroscopy, elemental analyses and FT-IR spectroscopy. Furthermore, the molecular structures of complexes 1a, 1d and 1g were determined by single crystal X-ray diffraction analysis. In the presence of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxyl) as co-oxidant and molecular oxygen (ambient air) as terminal oxidant, these dirhenium carbonyl complexes showed moderate catalytic activity for aerobic oxidation of secondary alcohols.
Hao, Zhiqiang,Li, Ning,Yan, Xinlong,Yue, Xiaohui,Liu, Kang,Liu, Huating,Han, Zhangang,Lin, Jin
p. 51 - 57
(2018/06/26)

Kinetic Resolution of sec-Thiols by Enantioselective Oxidation with Rationally Engineered 5-(Hydroxymethyl)furfural Oxidase
Various flavoprotein oxidases were recently shown to oxidize primary thiols. Herein, this reactivity is extended to sec-thiols by using structure-guided engineering of 5-(hydroxymethyl)furfural oxidase (HMFO). The variants obtained were employed for the oxidative kinetic resolution of racemic sec-thiols, thus yielding the corresponding thioketones and nonreacted R-configured thiols with excellent enantioselectivities (E≥200). The engineering strategy applied went beyond the classic approach of replacing bulky amino acid residues with smaller ones, as the active site was additionally enlarged by a newly introduced Thr residue. This residue established a hydrogen-bonding interaction with the substrates, as verified in the crystal structure of the variant. These strategies unlocked HMFO variants for the enantioselective oxidation of a range of sec-thiols.
Pickl, Mathias,Swoboda, Alexander,Romero, Elvira,Winkler, Christoph K.,Binda, Claudia,Mattevi, Andrea,Faber, Kurt,Fraaije, Marco W.
p. 2864 - 2868
(2018/03/08)

Regio- and chemoselective rearrangement of terminal epoxides into methyl alkyl and aryl ketones
The development of the highly active pincer-type rhodium catalyst 2 for the nucleophilic Meinwald rearrangement of functionalised terminal epoxides into methyl ketones under mild conditions is presented. An excellent regio- and chemoselectivity is obtained for the first time for aryl oxiranes.
Tian, Yingying,Jürgens, Eva,Kunz, Doris
p. 11340 - 11343
(2018/10/31)

Oxidation of Tertiary Aromatic Alcohols to Ketones in Water
A new rosin-based amphiphile enables the oxidation of tertiary aromatic alcohols in water under mild conditions. The oxidation process is mediated by β-scission of alkoxy radicals. Our catalyst system including the surfactant, catalysts, and water can be easily recycled within the same reaction vial. (Figure presented.).
Chen, Dengfeng,Zhang, Yuchen,Pan, Xingyu,Wang, Fei,Huang, Shenlin
supporting information
p. 3607 - 3612
(2018/09/18)

Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction
Heterocycles based on piperidine and pyrrolidine are key moieties in natural products and pharmaceutically active molecules. A novel multi-enzymatic approach based on the combination of a lipase with an α,ω-diamine transaminase is reported, opening up the synthesis, isolation and characterisation of a broad range of 2-substituted N-heterocycle alkaloids.
Galman, James L.,Slabu, Iustina,Parmeggiani, Fabio,Turner, Nicholas J.
supporting information
p. 11316 - 11319
(2018/10/24)

Biomimetic Oxidative Deamination Catalysis via ortho-Naphthoquinone-Catalyzed Aerobic Oxidation Strategy
An ortho-naphthoquinone-catalyzed oxidative deamination reaction has been developed where the molecular oxygen and water serve as the sole oxidant and nucleophile. The current aerobic deamination reaction proceeds via the ketimine formation between ortho-naphthoquinones and amines followed by the prototropic rearrangement and hydrolysis by water, representing a biomimetic oxidative deamination of amine species in the human body by the liver and kidneys. The compatibility of ortho-naphthoquinone organocatalysts with molecular oxygen and water opens up a new biomimetic catalyst system that can function as versatile deaminases for a variety of amine-containing molecules such as amino acids and DNA nuclear bases.
Golime, Gangadhararao,Bogonda, Ganganna,Kim, Hun Young,Oh, Kyungsoo
p. 4986 - 4990
(2018/05/14)

Pd(II)-Catalyzed Denitrogenative and Desulfinative Addition of Arylsulfonyl Hydrazides with Nitriles
A Pd(II)-catalyzed denitrogenative and desulfinative addition of arylsulfonyl hydrazides with nitriles has been successfully achieved under mild conditions. This transformation is a new method for the addition reaction to nitriles with arylsulfonyl hydrazides as arylating agent, thus providing an alternative synthesis of aryl ketones. The reported addition reaction is tolerant to many common functional groups, and works well in the presence of electron-donating and electron-withdrawing substituents. Notably, the reported denitrogenative and desulfinative addition was also appropriate for alkyl nitriles, making this newly developed transformation attractive.
Meng, Mengting,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
p. 3275 - 3284
(2018/03/25)

Design and Assembly of a Chiral Metallosalen-Based Octahedral Coordination Cage for Supramolecular Asymmetric Catalysis
Supramolecular containers featuring both high catalytic activity and high enantioselectivity represent a design challenge of practical importance. Herein, it is demonstrated that a chiral octahedral coordination cage can be constructed by using twelve enantiopure Mn(salen)-derived dicarboxylic acids as linear linkers and six Zn4-p-tert-butylsulfonylcalix[4]arene clusters as tetravalent four-connected vertices. The porous cage features a large hydrophobic cavity (≈3944 ?3) decorated with catalytically active metallosalen species and is shown to be an efficient and recyclable asymmetric catalyst for the oxidative kinetic resolution of racemic secondary alcohols and the epoxidation of olefins with up to >99 % enantiomeric excess. The cage architecture not only prevents intermolecular deactivation and stabilizes the Mn(salen) catalysts but also encapsulates substrates and concentrates reactants in the cavity, resulting in enhanced reactivity and enantioselectivity relative to the free metallosalen catalyst.
Tan, Chunxia,Jiao, Jingjing,Li, Zijian,Liu, Yan,Han, Xing,Cui, Yong
supporting information
p. 2085 - 2090
(2018/02/06)

Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains
Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents.
Cvijeti?, Ilija N.,Verbi?, Tatjana ?.,Ernesto de Resende, Pedro,Stapleton, Paul,Gibbons, Simon,Jurani?, Ivan O.,Drakuli?, Branko J.,Zloh, Mire
p. 1474 - 1488
(2017/11/17)

Tropylium Ion Catalyzes Hydration Reactions of Alkynes
The hydration of alkynes is one of the most atom-economic and versatile synthetic protocols to access carbonyl compounds. This fundamental reaction, however, often requires transition-metal catalysts or harsh reaction conditions to promote the addition of water to the carbon–carbon triple bond. In this work, it is demonstrated that the non-benzenoid aromatic tropylium ion can be used as an organic Lewis acid promoter for the hydration of alkynes under simple reaction conditions with excellent outcomes.
Oss, Giulia,Ho, Junming,Nguyen, Thanh Vinh
supporting information
p. 3974 - 3981
(2018/08/17)

Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation
A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.
Liu, Sensheng,Liu, Huan,Zhou, Haifeng,Liu, Qixing,Lv, Jinliang
supporting information
p. 1110 - 1113
(2018/02/23)

Easy Access to Enantiopure (S)- and (R)-Aryl Alkyl Alcohols by a Combination of Gold(III)-Catalyzed Alkyne Hydration and Enzymatic Reduction
Chemoenzymatic one-pot processes based on the combination of metal catalysis and biocatalysis open up highly attractive perspectives regarding the production of enantiopure compounds. By combining a gold-catalyzed hydration reaction with an enzymatic reduction, we present a straightforward and atom-economical chemoenzymatic method for the synthesis of secondary alcohols with excellent optical purity. Efficient cofactor recycling exploits the solvent of the metal-catalyzed step as an auxiliary substrate for the enzymatic step.
Schaaf, Patricia,Gojic, Vladimir,Bayer, Thomas,Rudroff, Florian,Schnürch, Michael,Mihovilovic, Marko D.
p. 920 - 924
(2018/02/23)

One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis
A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF3SO3H and a fluorinated chiral diamine Ru(ii) complex in aqueous CF3CH2OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.
Liu, Huan,Liu, Sensheng,Zhou, Haifeng,Liu, Qixing,Wang, Chunqin
p. 14829 - 14832
(2018/04/30)

Controlled Exchange of Achiral Linkers with Chiral Linkers in Zr-Based UiO-68 Metal-Organic Framework
The development of highly robust heterogeneous catalysts for broad asymmetric reactions has always been a subject of interest, but it remains a synthetic challenge. Here we demonstrated that highly stable metal-organic frameworks (MOFs) with potentially acid-labile chiral catalysts can be synthesized via postsynthetic exchange. Through a one- or two-step ligand exchange, a series of asymmetric metallosalen catalysts with the same or different metal centers are incorporated into a Zr-based UiO-68 MOF to form single- and mixed-M(salen) linker crystals, which cannot be accomplished by direct solvothermal synthesis. The resulting MOFs have been characterized by a variety of techniques including single-crystal X-ray diffraction, N2 sorption, CD, and SEM/TEM-EDS mapping. The single-M(salen) linker MOFs are active and efficient catalysts for asymmetric cyanosilylation of aldehydes, ring-opening of epoxides, oxidative kinetic resolution of secondary alcohols, and aminolysis of stilbene oxide, and the mixed-M(salen) linker variants are active for sequential asymmetric alkene epoxidation/epoxide ring-opening reactions. The chiral MOF catalysts are highly enantioselective and completely heterogeneous and recyclable, making them attractive catalysts for eco-friendly synthesis of fine chemicals. This work not only advances UiO-type MOFs as a new platform for heterogeneous asymmetric catalysis in a variety of syntheses but also provides an attractive strategy for designing robust and versatile heterogeneous catalysts.
Tan, Chunxia,Han, Xing,Li, Zijian,Liu, Yan,Cui, Yong
supporting information
p. 16229 - 16236
(2018/11/27)

Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases
A one-pot/two-step bienzymatic asymmetric amination of secondary alcohols is disclosed. The approach is based on a sequential strategy involving the use of a laccase/TEMPO catalytic system for the oxidation of alcohols into ketone intermediates, and their following transformation into optically enriched amines by using transaminases. Individual optimizations of the oxidation and biotransamination reactions have been carried out, studying later their applicability in a concurrent process. Therefore, 17 racemic (hetero) aromatic sec-alcohols with different substitutions in the aromatic ring have been converted into enantioenriched amines with good to excellent selectivities (90-99% ee) and conversion values (67-99%). The scalability of the process was also demonstrated when two different amine donors were used in the transamination step, such as isopropylamine and cis-2-buten-1,4-diamine. Satisfyingly, both sacrificial amine donors can shift the equilibrium toward the amine formation, leading to the corresponding isolated enantioenriched amines with good to excellent results.
Martínez-Montero, Lía,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
supporting information
p. 474 - 480
(2017/06/23)

Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules
A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.
Liu, Binbin,Jin, Fengli,Wang, Tianjiao,Yuan, Xiaorong,Han, Wei
supporting information
p. 12712 - 12717
(2017/09/11)

Metal-free oxidation of secondary benzylic alcohols using aqueous TBHP
We report a simple, yet efficient metal-free oxidation of secondary benzylic alcohols in the presence of t-butyl hydroperoxide (70% TBHP) with high yields of up to 98%. This type of reaction can be carried out using a wide variety of substrates, requires no other organic solvent, and proves to be tolerant toward a variety of different functional groups.
Wu, Jianglong,Liu, Yan,Ma, Xiaowei,Liu, Ping,Gu, Chengzhi,Dai, Bin
supporting information
p. 1747 - 1758
(2016/10/30)

Synthesis method for methyl-3'-bromine-[1,1'-biphenyl]-3-carboxylic acid formic acid
The invention discloses a synthesis method for methyl-3'-bromine-[1,1'-biphenyl]-3-carboxylic acid formic acid, and belongs to the technical field of organic chemistry.The method comprises the steps that benzene is used as a raw material and mixed with acetic anhydride and aluminum chloride for a reaction, then, concentrated nitric acid and concentrated sulfuric acid are added for a nitration reaction, the reaction product is sufficiently mixed with liquid bromine under the effect of iron powder, the mixture is placed in a reaction kettle, dimethyl carbonate and zirconium dioxide powder are added, boron trifluoride is introduced for a reaction, heating distillation is carried out under the oxidation of potassium permanganate and glacial acetic acid, ice water and zinc powder are added and mixed, standing decompression and suction filtration are performed, and the product is obtained.The synthesis method has the advantages that synthetic conditions are simple, few by-products are produced in the synthetic process, the cost is 5% or more lower than the cost of other methods, the obtained product is high in purity, and the yield is 15.5% or more higher than that of the other methods.
-
(2016/11/14)

Ketone synthesis method through alkyne hydrolysis
The invention discloses a ketone synthesis method through alkyne hydrolysis. The method comprises the following steps: adding alkyne, a catalyst [(IPr)AuCl], a solvent methanol, and water into a reactor, carrying out reactions for several hours at a temperature of 110 to 120 DEG C, cooling to the room temperature, carrying out rotary evaporation to remove the solvent, and performing column separation to obtain target compounds. Compared with conventional ionic gold catalyst, the provided method directly uses gold chloride [(IPr)AuCl] as the catalyst, alkyne is hydrolyzed into ketone, the yield is high, the selectivity is complete, and thus the method has an important meaning for organic synthesis and environment protection.
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Paragraph 0058-0061

(2017/05/02)