光氧化催化的 N-丙烯酰基-2-芳基苯并咪唑自由基二氟甲基化/环化反应，获得 CF2H 取代的苯并咪唑并[2,1-a]异喹啉-6(5H)-酮。

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-10-09 DOI:10.1039/d4ob01413h

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

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引用次数: 0

摘要

利用二氟甲基三苯基溴化鏻盐作为 -CF2H 基团的前体，在温和条件下开发了一种高效的可见光促进级联二氟甲基化/环化反应，以获得各种 CF2H 取代的苯并咪唑并[2,1-a]异喹啉-6(5H)-酮。该方案利用了一种易于获得且价格低廉的有机光催化剂，具有底物范围广、官能团耐受性好、产率高甚至极高以及操作步骤简单等优点。此外，还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。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones†

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Photoredox-catalysed radical difluoromethylation/cyclization of N-acryloyl-2-arylbenzimidazole to access CF2H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones†

An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CF₂H-substituted benzimidazo[2,1-a]isoquinolin-6(5H)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the –CF₂H 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.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.