title: Thiol ester-boronic acid cross-coupling. Catalysis using alkylative activation of the palladium thiolate intermediate.
abstract: Thiol esters and boronic acids do not participate in cross-coupling in the presence of palladium catalysts. However, efficient palladium-catalyzed thiol ester-boronic acid cross-coupling is observed when simple alkylating agents are present. Alkylative conversion of the very stable palladium-thiolate bond to a labile palladium-thioether bond is presumed to be crucial to the catalysis. Of the systems studied, 4-halo-n-butyl thiol esters were most effective in this cross-coupling.
authors.affiliation: Emory University, Department of Chemistry, 1515 Pierce Drive, Atlanta, Georgia 30322, USA.
authors.forename: C
authors.initials: C
authors.lastname: Savarin
authors.forename: J
authors.initials: J
authors.lastname: Srogl
authors.forename: L S
authors.initials: LS
authors.lastname: Liebeskind
mesh_terms: D000478:Alkylation; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D009942:Organometallic Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; C415665:palladium thiolate