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.
boronic acid - pKa
- sulfonamides - lithiation - cross-coupling
