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Functionalization of some benzylthioarylboronic acids by benzylic lithiation of their N ‐butyldiethanolamine esters or lithium (triisopropoxy)borates
Author(s) -
Durka Krzysztof,
Kliś Tomasz,
Serwatowski Janusz,
Woźniak Krzysztof
Publication year - 2011
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1822
Subject(s) - chemistry , lithium diisopropylamide , electrophile , lithium (medication) , boron , surface modification , lithium atom , ring (chemistry) , medicinal chemistry , organic chemistry , stereochemistry , ion , catalysis , medicine , ionization , endocrinology , deprotonation
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.