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Para-Selective Borylation of Monosubstituted Benzenes Using a Transient Mediator

revised on 02.11.2019, 16:03 and posted on 07.11.2019, 22:33 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.


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Shanghai Institute of Organic Chemistry



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Declaration of Conflict of Interest

The authors declare no conflict of interest.