Functionalization of some benzylthioarylboronic acids by benzylic lithiation of their N‐butyldiethanolamine esters or lithium (triisopropoxy)borates |
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| Authors: | Krzysztof Durka Tomasz Kliś Janusz Serwatowski Krzysztof Woźniak |
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| Institution: | 1. Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00‐664 Warsaw, Poland;2. Warsaw University, Faculty of Chemistry, Pasteura 1, 02‐093 Warsaw, Poland |
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| 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 arylboronic acids substituted in the benzylic position. Copyright © 2011 John Wiley & Sons, Ltd. |
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| Keywords: | lithiation boronic acid azaesters trialkoxyborates lithiated borates |
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