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copper-catalyzed Meerwein carboarylation of alkenes with anilines to form 3-benzyl-3-alkyloxindole

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Science China Chemistry 2015年第4期58卷 684-688页

作者： Shi Tang Dong Zhou Youlin Deng Zhihao Li You Yang Jianguang He Yingchun Wang College of Chemistry and Chemical Engineering Central South University College of Chemistry and Chemical Engineering Jishou University Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources(Ministry of Education of China) Guangxi Normal University

A simple and direct route for double C–C bond formation by copper-catalyzed Meerwein carboarylation process has been developed. In the presence of Cu I(5 mol%), tert-butyl nitrite and anilines, a wide variety of N-arylacrylamides underwent tandem Meerwein arylation/C–H cyclization to produce pharmaceutically important 3-benzyl-3-alkyloxindole in moderate to good yield.

关键词： radical reaction C-H cyclization Meerwein arylation oxindole copper-catalyzed

copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters for synthesis of functionalized 2,3-allenoates

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Chinese Chemical Letters 2023年第9期34卷 151-155页

作者： Qi Li Zi-Lu Wang Yun-He Xu Department of Chemistry University of Science and Technology of ChinaHefei 230026China

Herein,copper-catalyzed 1,4-protosilylation and 1,4-protoborylation of enynic orthoesters have been *** enynic orthoesters as precursors of unstable enynic esters were applied to produce the functionalized 2,3-allenoate ***,the asymmetric 1,4-protosilylation of enynic orthoesters with Ph Me2Si-Bpin was also *** chiral monopyridine imidazoline ligand was efficient to provide the asymmetric 1,4-protosilylation products with high enantioselectivity.

关键词： copper-catalyzed 1,4-Protosilylation 1,4-Protoborylation 2,3-Allenoate Enynic orthoesters

copper-catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides

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Chinese Journal of Chemistry 2021年第4期39卷 859-865页

作者： Dong Yi Linying He Zhongyu Qi Zhijie Zhang Mengshun Li Ji Lu Jun Wei Xi Du Qiang Fu Siping Wei Department of Medicinal Chemistry School of PharmacySouthwest Medical UniversityLuzhouSichuan 646000China People’s Hospital of Xinjin District ChengduSichuan 611430China School of Pharmacy Binzhou Medical UniversityYantaiShandong 264003China Central Nervous System Drug Key Laboratory of Sichuan Province LuzhouSichuan 646000Chino

Main observation and conclusion Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type ***,carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen,is scarce and ***,we report alkoxy radical,which was generated from alkyl radical and dioxygen,mediated selective cleavage of unstrained carbon-carbon bond for the oxysulfonylation of 1,1-disubstituted alkenes,providing facile access to a variety of valuableβ-keto *** experiments indicated alkoxy radical intermediate that underwent subsequent regioselectiveβ-scission might be involved in the reaction and preliminary computational studies were conducted to provide a detailed explanation on the regioselectivity of the C-C bond ***,the strategy was successfully applied for constructing uneasily obtained architecturally intriguing molecules.

关键词： Carbon-carbon cleavage Alkoxy radical copper-catalyzed 1,1-Disubstituted alkenes Sulfonyl hydrazides

copper-catalyzed Highly Enantioselective 1,4-Protoboration of Terminal 1,3-Dienes

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CCS Chemistry 2022年第5期4卷 1545-1556页

作者： Qitao Guan Yuqi Ji Qian Zhao Chun Zhang Institute of Molecular Plus Tianjin Key Laboratory of Molecular Optoelectronic ScienceDepartment of ChemistrySchool of ScienceTianjin UniversityTianjin 300072

The copper-catalyzed,highly enantioselective 1,4-protoboration of terminal 1,3-dienes with proton source and B2Pin2 has been *** allylic boronate reagents,which are significant precursors for many well-established transformations,were prepared by this novel method with good functional group tolerance and *** studies indicated the products could be used as versatile precursors for asymmetric transformations and natural products *** mechanism of this reaction was investigated by control and reaction monitoring experiments.

关键词： copper-catalyzed enantioselectivity regioselectivity conjugated addition chiral borated allylic reagents

Ligand-free copper-catalyzed Synthesis of Symmetrical Diynes from 1,1-Dibromo-1 -alkenes

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Chinese Journal of Chemistry 2011年第3期29卷 592-594页

作者： Jin, Hui Kuang, Chunxiang Department of Chemistry Tongji University Shanghai 200092 China

Symmetrical diynes were synthesized by ligand-free copper-catalyzed homocoupling reaction of 1,1-dibromo-1- alkenes using a DBU/DMSO system at room temperature in good to excellent yields.

关键词： symmetrical diynes copper-catalyzed 1,1-dibromo-l-alkenes ligand-free homocoupling

Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via copper-catalyzed Cyclization of Alkenes

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Chinese Journal of Chemistry 2016年第11期34卷 1076-1080页

作者： Sai-Hu Cai Bing-Chao Da Jia-Hui Zhou Yun-He Xu Teck-Peng Loh Department of Chemistry University of Science and Technology of China Hefei Anhui 230026 China DiVision of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 637371 Singapore

An efficient methodology for the stereoselective synthesis of cis-2,5-disubstituted pyrrolidines using copper catalyst was developed. The corresponding cis-2,5-disubstituted pyrrolidines could be obtained in reasonable yields and with good stereoselectivities in the presence of 4,4＇-di-tert-butyl-2,2＇-bipyridine as ligand and l-methyl-2-pyrrolidinone as solvent.

关键词： stereoselectivity pyrrolidines copper-catalyzed cyclization

Microwave-assisted chemoselective copper-catalyzed amination of o-chloro and o-bromobenzoic acids using aromatic amines under solvent free conditions

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Chinese Chemical Letters 2009年第7期20卷 784-788页

作者： Yaghoub Sarrafi Manijeh Mohadeszadeh Kamal Alimohammadi Faculty of Chemistry Mazandaran UniversityBabolsarIran

copper-catalyzed synthesis of N-aryl anthranilic acid derivatives using effective amination of 2-chloro and 2-bromobenzoic acid under microwave irradiation is reported. Some of the advantages of this method are high chemoselectivity, short reaction times, ease of work up procedure and elimination of the need for acid protection. 2009 Published by Elsevier B.V. on behalf of Chinese Chemical Society.

关键词： Microwave-assisted copper-catalyzed Solvent free Amination N-Aryl anthranilic acid

Practical copper-catalyzed N-arylation of amines with 20% aqueous solution of n-Bu_4NOH

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Chinese Chemical Letters 2012年第3期23卷 301-304页

作者： Hamidreza Molaei Mohammad Mehdi Ghanbari Department of Chemistry Sarvestan BranchIslamic Azad UniversitySarvestanIran

N-Arylation of a wide variety of amines with phenylboronic acid catalyzed by copper acetate under 20%aqueous solution of n-Bu_4NOH was accomplished in good to excellent yields（up to 92%） and substrate conversions（u... 详细信息

关键词： copper-catalyzed N-Arylation Phenylboronic acid Amines

copper-catalyzed C-C(O)C Bond Cleavage of Monoalkylated β-Diketone: Synthesis of α,β-Unsaturated Ketones

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International Journal of Organic Chemistry 2023年第2期13卷 41-49页

作者： Tony Wheellyam Pouambeka Victor N’goka Narcisse Nicaise Obaya Guy Crépin Enoua Hubert Makomo Qian Zhan Laboratory of Plant and Life Chemistry Unit: Equipe de Chimie Organique et Analytique des Substances Bioactives Faculty of Science and Technology Marien Ngouabi University Brazzaville The Republic of Congo Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis Faculty of Chemistry Northeast Normal University Changchun China

A new and simple route for the synthesis of α,β-unsaturated ketones via cleavage of the C-C(O)C single bond of monoalkylated β-diketone has been described. The reaction was catalyzed by copper, a cheap transition metal in a weakly basic medium (K3PO4) at room temperature. To carry out this study, we first had to synthesize the monoalkylated β-diketones 1. Afterwards, α,β-unsaturated ketones 2 were obtained with high yields around 80%. Finally, all the products were characterized by 1H NMR, 13C NMR, and HRMS spectra. .

关键词： Monoalkylated β-diketone α β-Unsaturated Ketones copper-catalyzed C-C(O)C Bond Cleavage