Copper-mediated, palladium-catalyzed coupling of thiol esters with aliphatic organoboron reagents.
Thiol esters and B-alkyl-9-BBN derivatives couple in the presence of a copper(I) carboxylate mediator and a palladium catalyst. In contrast to copper-mediated, palladium-catalyzed cross-couplings of thioorganics with boronic acids, the current coupling reaction of 9-BBN derivatives is facilitated by the addition of a base such as Cs(2)CO(3). Under optimized conditions, a variety of thiol esters react with different B-alkyl-9-BBN derivatives giving ketones in moderate to excellent yields.
Yu
Ying
Y
Emory University, Department of Chemistry, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Liebeskind
Lanny S
LS
D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D001896:Boron Compounds; D004952:Esters; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; D010165:Palladium; D003300:Copper