Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 11, Pages 7386-7398Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00792
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Funding
- NSFC [21662043, 21572197, U1702286]
- Program for Changjiang Scholars and Innovative Research Teams in Universities [IRT17R94]
- IRTSTYN
- NSF of Yunnan Province [2019FY003010]
- DongLu Scholar
- YunLing Scholar Program
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Herein, we disclose the synthesis of diaryl selenides through an unexpected C-Se coupling between aryl benzyl selenoxides and phenols. The synthetic significance of the method is that it provides a mild, rapid, and metal-free access to organoselenides in high yields with excellent functional group tolerance. This coupling of aryl benzyl selenoxides reveals a completely new reaction possibility compared with aryl sulfoxides. We also probed the reaction mechanism of this unexpected transformation through experimental studies and revealed a special Se(IV)-Se(III)-Se(II) reaction pathway.
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