A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides.
The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
Fernández-Rodríguez
Manuel A
MA
Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
Hartwig
John F
JF
D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007454:Iodides / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013696:Temperature
D001965:Bromides; D002712:Chlorides; D004987:Ethers; D007454:Iodides; D013438:Sulfhydryl Compounds; D010165:Palladium