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Copper-catalyzed oxidative CH bond functionalization of N-allylbenzamide for CN and CC bond formation
Institution:1. State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, China;2. Merro Pharmaceutical Co., Ltd., Dalian 116036, China;1. Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China;2. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, China;1. College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, China;2. College of Pharmaceutical Science, Zhejiang University, Hangzhou 310058, China;1. Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, Henan, China;2. Xiangya School of Public Health, Central South University, Changsha 410078, Hunan, China;3. School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, Hunan, China
Abstract:Csingle bondH bond functionalization for Csingle bondN and Csingle bondC bond formations via cross-dehydrogenative coupling (CDC) of N-allylbenzamides with indole as amine source has been developed under a copper-catalyzed condition. To the best of our knowledge, these are the first examples in which different classes of N-containing compounds were directly prepared from the readily available N-allylbenzamides using an inexpensive catalyst-oxidant (CuSO4/TBHP) system. Further, it was applied for the synthesis of α-substituted N-allylbenzamides by using Grignard reagent as nucleophiles.
Keywords:Copper-catalyzed  Oxidative coupling  CDC coupling  Grignard reaction
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