摘要
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 paraborylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.
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 paraborylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.
基金
supported by Shanghai Institute of Organic Chemistry,State Key Laboratory of Organometallic Chemistry,the National Natural Science Foundation of China(21890722,21702109,11811530637)
the Natural Science Foundation of Tianjin City(18JCYBJC21400)
the Fundamental Research Funds for the Central Universities(63191515,63196021,63191523).
