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Para-Selective Borylation of Monosubstituted Benzenes Using a Transient Mediator

preprint
revised on 02.11.2019 and posted on 07.11.2019 by Jie Wu, Zengwei Wang, Xiao-Yue Chen, Yichen Wu, Daoming Wang, Qian Peng, Peng Wang
Herein, we conceptualized a transient mediator approach that has the capability of para-selective C–H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.

History

Email Address of Submitting Author

pengwang@sioc.ac.cn

Institution

Shanghai Institute of Organic Chemistry

Country

China

ORCID For Submitting Author

0000-0002-6442-3008

Declaration of Conflict of Interest

The authors declare no conflict of interest.

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