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

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

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 KO t Bu initiates an electron transfer process and generates an ary...

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Veröffentlicht in:Journal of organic chemistry 2022-09, Vol.87 (18), p.12323-12333
Hauptverfasser: Kazi, Imran, Nandy, Anuradha, Selvam, Raji, Sekar, Govindasamy
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container_issue 18
container_start_page 12323
container_title Journal of organic chemistry
container_volume 87
creator Kazi, Imran
Nandy, Anuradha
Selvam, Raji
Sekar, Govindasamy
description 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 KO t Bu 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 KO t Bu. This methodology has been successfully utilized to synthesize antileishmanial agents.
doi_str_mv 10.1021/acs.joc.2c01548
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title Halogen Bond-Activated Visible-Light-Mediated Regioselective C–H Arylation of 2‑Phenylimidazo-[1,2‑a]pyridines
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