Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates.
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.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Bernardi
Carmem R
CR