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Synlett 2004(5): 0892-0894
DOI: 10.1055/s-2004-817758
DOI: 10.1055/s-2004-817758
LETTER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Sulfonyl Chlorides of Phenylboronic Acids
Further Information
Received
26 November 2003
Publication Date:
10 February 2004 (online)
Publication History
Publication Date:
10 February 2004 (online)
Abstract
Sulfonyl chlorides of phenylboronic esters have been made available by selective lithiation of bromo N-methyl-diethanolamine phenylboronates to give lithium sulfinyl phenylboronates as intermediates. Oxidations with N-chlorosuccinimide give the target sulfonyl chlorides, which may be isolated or used in situ for further reactions. The novel reagents are useful in preparation of among other sulfonamides of phenylboronic acids for use in Pd(0) catalysed cross-couplings. They also hold potential as carbohydrate binders with physiological pKa.
Key words
boronic acid - pKa - sulfonamides - lithiation - cross-coupling
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