Copper-Catalyzed Aerobic Oxidative Cleavage of Unstrained Carbon-Carbon Bonds of 1,1-Disubstituted Alkenes with Sulfonyl Hydrazides  

作　　者：Dong Yi Linying He Zhongyu Qi Zhijie Zhang Mengshun Li Ji Lu Jun Wei Xi Du Qiang Fu Siping Wei 

机构地区：[1]Department of Medicinal Chemistry,School of Pharmacy,Southwest Medical University,Luzhou,Sichuan 646000,China [2]People’s Hospital of Xinjin District,Chengdu,Sichuan 611430,China [3]School of Pharmacy,Binzhou Medical University,Yantai,Shandong 264003,China [4]Central Nervous System Drug Key Laboratory of Sichuan Province,Luzhou,Sichuan 646000,Chino

出　　处：《Chinese Journal of Chemistry》2021年第4期859-865,共7页中国化学（英文版）

基　　金：Fund of Luzhou Government and Southwest Medical University(Nos.2019LZXNYDJ28,2018LZXNYD-ZK33,2018LZXNYD-ZK39);the Open Project of Central Nervous System Drug Key Laboratory of Sichuan Province(No.200023-01SZ);the research fund of Southwest Medical University(Nos.2017-ZRZD-020 and 2017-ZRQN-031).

摘　　要：Main observation and conclusion Alkoxy radical-mediated carbon-carbon bond cleavages have emerged as a powerful strategy to complement traditional ionic-type transformations.However,carbon-carbon cleavage reaction triggered by alkoxy radical intermediate derived from the combination of alkyl radical and dioxygen,is scarce and underdeveloped.Herein,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 sulfones.Mechanistic 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 cleavage.Notably,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 

分 类 号：O62[理学—有机化学]