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
收藏
页码：12323 / 12333
页数：11
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