Selenium Radical Mediated Cascade Cyclization: Concise Synthesis of Selenated Benzofurans (Benzothiophenes)

Presented in this work is a novel methodology for the synthesis of selenated benzofurans (or benzothiophenes) via AgNO2-catalyzed radical cyclization of 2-alkynylanisoles (or 2-alkynylthioanisoles), Se powder, and arylboronic acids. This method enables the construction of a benzofuran (benzothiophen...

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Bibliographic Details
Published in:Organic letters 2019-09, Vol.21 (17), p.6710-6714
Main Authors: An, Cui, Li, Chen-Yuan, Huang, Xiao-Bo, Gao, Wen-Xia, Zhou, Yun-Bing, Liu, Miao-Chang, Wu, Hua-Yue
Format: Article
Language:English
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Summary:Presented in this work is a novel methodology for the synthesis of selenated benzofurans (or benzothiophenes) via AgNO2-catalyzed radical cyclization of 2-alkynylanisoles (or 2-alkynylthioanisoles), Se powder, and arylboronic acids. This method enables the construction of a benzofuran (benzothiophene) ring, two C–Se bonds, and a C–O­(S) bond as well as the cleavage of a C–O­(S) bond in a single step. Preliminary mechanistic studies imply that the AgNO2-catalyzed cyclization proceeds via an aryl selenium radical intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02315