Benzoyl cyanide, a general radical acylating reagent for photoredox-catalyzed benzylic site-selective acylation reactions  

作　　者：Zhaodong Zhu Jingjing Wu 

机构地区：[1]Frontiers Science Center for Transformative Molecules,Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs,School of Chemistry and Chemical Engineering,Zhangjiang Institute for Advanced Study,Shanghai Jiao Tong University,Shanghai 200240,China

出　　处：《Science China Chemistry》2024年第11期3833-3843,共11页中国科学（化学英文版）

基　　金：supported by National Natural Science Foundation of China (NSFC);Youth program (Grant No: 22101173);Fundamental Research Funds for the Central Universities (23X010301599);“Thousand Talents Plan, Youth project”;startup funding from Shanghai Jiao Tong University (SJTU)。

摘　　要：Based on rational design, benzoyl cyanide, a well-known ionic acylating reagent, has been developed as a general radical acylating reagent for benzylic site-selective acylation reactions for the first time. Using visible-light photoredox-catalyzed single electron transfer(SET) and hydrogen atom transfer(HAT) strategies, two different direct benzylic C–H acylation reactions with high atom economy have been developed. This newly developed radical acylating reagent could also be used to achieve three component acyltrifluoromethylation of styrenes, which is usually challenging to achieve by other means. All of these reactions proceed under mild nickel-free and NHC-free conditions with high functional group tolerance. In addition, based on our detailed mechanistic experiments, the process of radical-radical cross-coupling mechanism was suggested for these transformations.

关 键 词：photoredox catalysis benzylic C–H acylation radical acylating reagent HAT catalysis acyltrifluoromethylation 

分 类 号：TQ421.12[化学工程]