Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.
Enantiomerically enriched potassium β-trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling reactions were carried out with various aryl- and hetaryl chlorides in good to excellent yields. Moreover, the diastereoselectivities were preserved throughout the Suzuki-Miyaura cross-coupling reactions.
Molander
Gary A
GA
Roy and Diana A. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Shin
Inji
I
Jean-Gérard
Ludivine
L
D000577:Amides / Q000138:chemical synthesis*; D001896:Boron Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D017606:Chlorine Compounds / Q000737:chemistry*; D017611:Fluorine Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D017680:Potassium Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000577:Amides; D001896:Boron Compounds; D017606:Chlorine Compounds; D017611:Fluorine Compounds; D017680:Potassium Compounds; D010165:Palladium