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

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 to different functional groups has been tested. Mechanistic studies re...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 3; pp. 837 - 841
Main Authors Zhou, Bigui, Yuan, Zhiwei, Yu, Jingxun, Luan, Xinjun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 28.01.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NAPHTHOLS
FUNCTIONALIZATION
IODINE
PHENOLS
NITRATION
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Summary: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 to different functional groups has been tested. Mechanistic studies revealed that this domino reaction was possibly realized by the deiodination and tautomerization of the key dearomatized intermediate to generate a free phenolic O radical. Moreover, an anticancer agent 4 and an α-glucosidase inhibitor 5 with high bioactivities were successfully synthesized using this novel protocol.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04065