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可见光诱导的未活化烯烃的自由基级联二氟甲基化/环化反应:合成含CFH取代的多环咪唑类化合物

Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CFH-Substituted Polycyclic Imidazoles.

作者信息

Lin Sheng-Nan, Deng Yuanyuan, Zhong Hanxun, Mao Liu-Liang, Ji Cong-Bin, Zhu Xian-Hong, Zhang Xiaolan, Yang Bin-Miao

机构信息

College of Chemistry and Environment Science, Shangrao Normal University, Shangrao 334001, China.

Joint School of National University of Singapore and Tianjin University, Fuzhou 350207, China.

出版信息

ACS Omega. 2024 Jun 19;9(26):28129-28143. doi: 10.1021/acsomega.4c01177. eCollection 2024 Jul 2.

Abstract

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible and bench-stable difluoromethyltriphenylphosphonium bromide as the precursor of the -CFH group has been developed to afford CFH-substituted polycyclic imidazoles in moderate to good yields. This strategy, along with the construction of Csp-CFH/C-C bonds, is distinguished by mild conditions, no requirement of additives, simple operation, and wide substrate scope. In addition, the mechanistic experiments have indicated that the difluoromethyl radical pathway is essential for the methodology.

摘要

已开发出一种高效且温和的方法,使用易于获得且在实验室稳定的二氟甲基三苯基溴化鏻作为 -CFH 基团的前体,实现咪唑与未活化烯烃的可见光诱导自由基级联二氟甲基化/环化反应,以中等至良好的产率得到 CFH 取代的多环咪唑。该策略与 Csp-CFH/C-C 键的构建一起,具有条件温和、无需添加剂、操作简单和底物范围广的特点。此外,机理实验表明二氟甲基自由基途径对该方法至关重要。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fd0e/11223139/2fc054393871/ao4c01177_0001.jpg

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