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可见光驱动的异腈与 -(二氟甲基)二芳基锍盐的二氟甲基化反应:合成多种二氟甲基化菲啶和异喹啉。

Visible-Light-Driven Difluoromethylation of Isocyanides with -(Difluoromethyl)diarylsulfonium Salt: Access to a Wide Variety of Difluoromethylated Phenanthridines and Isoquinolines.

作者信息

Qin Wen-Bing, Xiong Wei, Li Xin, Chen Jia-Yi, Lin Li-Ting, Wong Henry N C, Liu Guo-Kai

机构信息

School of Pharmaceutical Sciences, Shenzhen University Health Science Centre, Shenzhen University, 3688 Nanhai Avenue, Shenzhen 518060, China.

Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China.

出版信息

J Org Chem. 2020 Aug 21;85(16):10479-10487. doi: 10.1021/acs.joc.0c00816. Epub 2020 Jul 31.

Abstract

A highly efficient approach of visible-light-driven radical difluoromethylation of isocyanides to access a wide variety of difluoromethylated phenanthridines and isoquinolines is herein described. Electrophilic -(difluoromethyl)diarylsulfonium salt proved to be a good difluoromethyl radical precursor under photoredox catalysis. A broad range of isocyanides were tolerated to furnish the corresponding difluoromethylated phenanthridines, isoquinolines, furo[3,2-]pyridine, and pyrido[3,4-]indole in moderate to excellent yields under mild conditions. A plausible mechanism was also proposed.

摘要

本文描述了一种高效的可见光驱动异腈自由基二氟甲基化方法,可用于制备多种二氟甲基化菲啶和异喹啉。亲电的 -(二氟甲基)二芳基锍盐在光氧化还原催化下被证明是一种良好的二氟甲基自由基前体。在温和条件下,多种异腈能够耐受,以中等至优异的产率提供相应的二氟甲基化菲啶、异喹啉、呋喃并[3,2-]吡啶和吡啶并[3,4-]吲哚。还提出了一个合理的机理。

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