Organic Chemistry

Para-Selective Borylation of Monosubstituted Benzenes Using a Transient Mediator

Authors

Abstract

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.

Content

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Supplementary material

Thumbnail image of SI paraBorylationV2.pdf
SI paraBorylationV2
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Graphic
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Proposed Mechanism