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(C 3 H 5 )(dppb), Cs 2 CO 3 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.