Palladium-catalysed Suzuki cross-coupling of primary alkylboronic acids with alkenyl halides

Abstract

The Suzuki reaction of primary alkylboronic acids with alkenyl halides proceeds nicely using the air-stable catalyst PdCl(C3H 5)(dppb), Cs2CO3 as base and toluene or xylene as solvent. A minor effect of the substituent position of the alkenyl bromide was observed. Quite similar yields were observed in the presence of α- or β-substituted alkenyl bromides such as 2-bromobut-1-ene or 1-bromo-2-methylprop-1-ene with this catalyst. This reaction proceeded with a variety of alkylboronic acids such as 2-phenylethylboronic acid or n-octylboronic acid. Lower yields of coupling products were obtained in the presence of an alkenyl chloride. Copyright © 2008 John Wiley & Sons, Ltd.