The importance of secondary benzylic alcohol motif is clearly evident from its presence in biologically active compounds and its application as an intermediate in organic synthesis. Although these compounds can be accessed by different methods, most of the current methods either permit only protected alcohols or tolerate limited functional groups. Therefore, the direct synthesis of this class of compounds is of great interest since the protection and deprotection steps can be avoided. Recently, our lab has developed a method to couple α-alkoxytrifluroborate compounds with aryl and heteroaryl electrophiles under photoredox/Ni dual catalysis. Herein we describe a method coupling alpha-hydroxy alkyltrifluoroborate(C-Sp3) with aryl halides (C-Sp2) under photoredox/Ni catalysis. This reaction gives the access to the direct synthesis of secondary benzylic alcohol under very mild conditions. Different functional group such as aldehyde, ketone, sulfone, sulfonamide and boronate can be tolerated under the developed conditions.

Cross-coupling of α-hydroxy alkyltrifluoroborate with aryl electrophiles under photoredox/Ni dual catalysis

254th National Meeting (2017)

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