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光氧化还原催化的 - 丙烯酰基 - 2 - 芳基苯并咪唑的自由基二氟甲基化/环化反应以合成含CFH取代的苯并咪唑并[2,1 - ]异喹啉 - 6(5) - 酮。

Photoredox-catalysed radical difluoromethylation/cyclization of -acryloyl-2-arylbenzimidazole to access CFH-substituted benzimidazo[2,1-]isoquinolin-6(5)-ones.

作者信息

Yuan Jinwei, Qu Hongzhao, Jia Wenfeng, Li Jinling, Yang Liangru, Xiao Yongmei, Yin Yanli, Qu Lingbo

机构信息

School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001, China.

College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China.

出版信息

Org Biomol Chem. 2024 Nov 21;22(45):8904-8915. doi: 10.1039/d4ob01413h.

Abstract

An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CFH-substituted benzimidazo[2,1-]isoquinolin-6(5)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the -CFH group under mild conditions. This protocol utilized an easily accessible and inexpensive organophotocatalyst, offering the benefits of a broad substrate scope, good functional group tolerance, and good to excellent yields, in addition to a simple operational procedure. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that a radical pathway constitutes a single electron transfer (SET) procedure.

摘要

开发了一种高效的可见光促进的串联二氟甲基化/环化反应,在温和条件下,以二氟甲基三苯基溴化鏻盐作为-CFH基团的前体,可得到各种CFH取代的苯并咪唑并[2,1-]异喹啉-6(5)-酮。该方法使用了一种易于获得且价格低廉的有机光催化剂,除了操作简单外,还具有底物范围广、官能团耐受性好、产率良好至优异等优点。此外,对反应机理进行了研究,结果表明自由基途径构成了单电子转移(SET)过程。

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