Suzuki-Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles.
We have previously reported that the palladium-catalyzed cross-coupling reaction of potassium vinyltrifluoroborate with aryl electrophiles proceeds with good yields. Herein, we describe recent progress in optimizing the reaction, as well as outlining the scope and limitations of the reaction. The cross-coupling reaction can generally be effected using 2 mol % of PdCl2 and 6 mol % of PPh3 as a catalyst system in THF/H2O with Cs2CO3 as a base. Moderate to good yields are obtained in the presence of a variety of functional groups.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Brown
Adam R
AR
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011188:Potassium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D001881:Borates; D002586:Cesium; D010165:Palladium; C008756:palladium chloride; D011188:Potassium