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Copper(I)-Catalyzed Chemoselective Reduction of Benzofuran-2-yl Ketones to Alcohols with B2pin2 via a Domino-Borylation-Protodeboronation Strategy

Authors :
Qiuling Song
Weiguang Kong
Qingqing Xuan
Source :
The Journal of Organic Chemistry. 82:7602-7607
Publication Year :
2017
Publisher :
American Chemical Society (ACS), 2017.

Abstract

A novel copper(I)-catalyzed chemoselective reduction of the carbonyls of benzofuran-2-yl ketones over furan rings with B2pin2 has been developed. This reaction proceeded under mild conditions. High valuable secondary alcohol derivatives of benzofurans were obtained in good to excellent yields with a broad substrate scope. The mechanistic studies suggested that a domino-borylation-protodeboronation pathway was involved in this reaction.

Details

ISSN :
15206904 and 00223263
Volume :
82
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi...........4370d721b52d9ed1563718c57b713140
Full Text :
https://doi.org/10.1021/acs.joc.7b00596