Visible-Light-Promoted [3 + 2] Cyclization of Chalcones with 2-Mercaptobenzimidazoles: A Protocol for the Synthesis of Imidazo[2,1-]thiazoles.

Org Lett

Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi, Xinjiang 830017, People's Republic of China.

Published: May 2022

A visible-light-promoted [3 + 2] cyclization between chalcones and 2-mercaptobenzoimidazoles for the construction of diverse imidazo[2,1-]thiazoles via an electron-donor-acceptor (EDA) complex has been developed. This novel aminothiolation can be realized under only visible light irradiation without the aid of external photocatalysts, transition metals, and oxidants. Mechanistic investigations have revealed that the thiol anions and chalcones form EDA complexes, providing a novel strategy for the synthesis of imidazo[2,1-]thiazoles.

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http://dx.doi.org/10.1021/acs.orglett.2c00867DOI Listing

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