文献类型：期刊文献

英文题名：Photocatalytic C-H silylation of heteroarenes by using trialkylhydrosilanes

作者：Liu, Shihui[1,2];Pan, Peng[1,2];Fan, Huaqiang[1,2];Li, Hao[1,2];Wang, Wei[1,2,3];Zhang, Yongqiang[1,2]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, State Key Lab Bioengn Reactor, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[3]Univ Arizona, Dept Pharmacol & Toxicol, BIO5 Inst, Tucson, AZ 85721 USA

年份：2019

卷号：10

期号：13

起止页码：3817

外文期刊名：CHEMICAL SCIENCE

收录：;EI(收录号：20191306712431);WOS:【SCI-EXPANDED(收录号:WOS:000462795800013)，CCR-EXPANDED(收录号:WOS:000462795800013)】；

基金：Financial support of this research from the program of the National Natural Science Foundation of China (21738002 and 21572055, W. W. and 21602060 and 21871086, Y.-Q. Z.) is gratefully acknowledged. Acknowledgement is also made to the donors of the American Chemical Society Petroleum Research Fund for partial support of this research (PRF#: 57164-ND1).

语种：英文

外文关键词：Chemical stability

摘要：The efficient and selective C-H silylation of heteroarenes, especially the pharmaceutically relevant electron-deficient heteroarenes, represents a great challenge in organic synthesis. Herein we wish to report a distinctive visible light-promoted photocatalytic C-H silylation approach that enables the direct coupling of trialkylhydrosilanes with both electron-deficient and -rich heteroarenes as well as with cyano-substituted arenes in moderate to high yields and with good regioselectivity. The protocol features operational simplicity, mild reaction conditions, and the use of safe and readily available Na2S2O8, bis(trimethylsilyl) peroxide (BTMSPO) or (Pr3SiSH)-Pr-i as the radical initiators. Notably, the challenging bulky and inert trialkylhydrosilanes, such as (t-butyldimethyl) silane ((BuMe2SiH)-Bu-t) and (triisopropyl) silane ((Pr3SiH)-Pr-i), work smoothly with the protocol. Moreover, despite the higher stability of (BuMe2Si)-Bu-t silylation products, our studies revealed their great reactivity and versatility in diverse C-Si-based chemical transformations, providing an operationally simple, low-cost, and environmentally benign synthetic technology for molecule construction and elaboration.