Dearomatization/Deiodination of o-Iodophenolic Compounds with α,β-Unsaturated Imines for Accessing Benzofuran Derivatives

• DOI: 10.1021/acs.orglett.1c04065
• Publication Date: 2022-01-12T16:08:52Z
• Authors: Bigui Zhou; Zhiwei Yuan; Jingxun Yu; Xinjun Luan
• Keywords: Benzofuran

A dearomatization/deiodination/rearomatization strategy for the [3 + 2] cyclization of o-iodophenolic substrates with α,β-unsaturated imines to construct various dihydrobenzofuran-related skeletons has been established. Tolerance different functional groups tested. Mechanistic studies revealed that this domino reaction was possibly realized by deiodination and tautomerization key dearomatized intermediate generate a free phenolic O radical. Moreover, an anticancer agent 4 α-glucosidase inhibitor 5 high bioactivities were successfully synthesized using novel protocol.