Halogen Bond-Activated Visible-Light-Mediated Regioselective C-H Arylation of 2-Phenylimidazo-[1,2-a]pyridines

被引：11

作者：

Kazi, Imran ^{[1
]}

Nandy, Anuradha ^{[1
]}

Selvam, Raji ^{[1
]}

Sekar, Govindasamy ^{[1
]}

机构：

[1] Indian Inst Technol Madras, Dept Chem, Chennai 600036, Tamil Nadu, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 18期

关键词：

METAL-FREE ARYLATION; DIARYLIODONIUM SALTS; ARYL; HETEROCYCLES; FUNCTIONALIZATION; CATALYST; BENZENE; ACCESS; ARENE;

D O I：

10.1021/acs.joc.2c01548

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for transition metal-free halogen bond-assisted regioselective C-H arylation of 2-phenylimidazo-[1,2-a]pyridines under visible-light condition has been developed. The halogen bond between an aryl halide and base (KOBu)-Bu-t initiates an electron transfer process and generates an aryl radical, which catalyzes its coupling with 2-phenylimidazo-[1,2-a]pyridines to give arylated products in good yield. Several control experiments, density functional theory calculations, and ultraviolet-visible analysis indicate the presence of a halogen bond between an aryl halide and (KOBu)-Bu-t. This methodology has been successfully utilized to synthesize antileishmanial agents.

引用

页码：12323 / 12333

页数：11

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