title: Copper-mediated, palladium-catalyzed coupling of thiol esters with aliphatic organoboron reagents.
abstract: 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.
authors.affiliation: Emory University, Department of Chemistry, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
authors.forename: Ying
authors.initials: Y
authors.lastname: Yu
authors.forename: Lanny S
authors.initials: LS
authors.lastname: Liebeskind
mesh_terms: 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*
chemical_list: D001896:Boron Compounds; D004952:Esters; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; D010165:Palladium; D003300:Copper