Functionalization of some benzylthioarylboronic acids by benzylic lithiation of their N??butyldiethanolamine esters or lithium (triisopropoxy) borates

K Durka, T Kliś, J Serwatowski…

Index: Durka, Krzysztof; Klis, Tomasz; Serwatowski, Janusz; Wozniak, Krzysztof Applied Organometallic Chemistry, 2011 , vol. 25, # 9 p. 669 - 674

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Citation Number: 4

Abstract

Abstract The 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 ...