Abstract

AbstractThe reaction of benzylthioarylboronic acids protected as N‐butyldiethanolamine esters or as triisopropoxyborates with organolithium bases or lithium diisopropylamide (LDA) has been investigated. The benzylic lithiation occurs selectively using LDA at − 68 °C. The stability of the resultant borio‐lithio intermediates is strongly influenced by the position of the boron atom in the phenyl ring. The reaction with various electrophiles affords new arylboronic acids substituted in the benzylic position. Copyright © 2011 John Wiley & Sons, Ltd.

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