posted on 2002-10-30, 00:00authored byGary A. Molander, Carmem R. Bernardi
We have previously reported that the palladium-catalyzed cross-coupling reaction of air-stable
potassium alkenyltrifluoroborates with aryl halides and triflates proceeds readily with good yields.
Recent progress in outlining the scope and limitations of such reactions is described herein. The
palladium-catalyzed cross-coupling reaction of potassium alkenyltrifluoroborates with aryl and
heteroaryl halides and triflates proceeds readily with moderate to excellent yields. The alkenyl
cross-coupling reaction can generally be effected using 2 mol % of PdCl2(dppf)·CH2Cl2 as catalyst
in i-PrOH−H2O in the presence of t-BuNH2 as the base. A variety of functional groups are tolerated
in both partners, and the process is stereospecific with regard to the alkenyltrifluoroborate starting
material.