Palladium-catalyzed coupling of thiol esters with aryl and primary and secondary alkyl organoindium reagents.
Thiol esters and organoindium reagents undergo palladium-catalyzed cross-coupling under mild conditions to give ketones in moderate to excellent yields. Aryl and primary/secondary alkyl organoindium reagents can be used as coupling partners. This method has two advantages over the cross-coupling of thiol esters with boron and tin reagents: (1) no added copper reagent is required to mediate the reaction and (2) for the case of alkyl transfer, no added base is required to activate organoindium reagents for cross-coupling as is required for the coupling of alkyl boron reagents with thiol esters.
Fausett
Bryan W
BW
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Liebeskind
Lanny S
LS
D002384:Catalysis; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents; D007204:Indium / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D007204:Indium; D010165:Palladium