Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols.
The cross-coupling reaction of aryl chlorides with aliphatic and aromatic thiols catalyzed by palladium complexes of the strongly binding bisphosphine CyPF-tBu ligand (1) is reported. Most of the reactions catalyzed by complexes of ligand 1 occur with turnover numbers that exceed those of previous catalysts by two orders of magnitude. The reactions occur with excellent yields, broad scope and high tolerance of functional groups. Coupling of aryl halides with thiols in the presence of low loadings of catalysts derived from other Josiphos type ligands, as well as ligands of other structural types, are also described.
Fernández-Rodríguez
Manuel A
MA
Department of Chemistry, Yale University P.O. Box 208107, New Haven, CT 06520-8107, USA.
Shen
Qilong
Q
Hartwig
John F
JF
D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D010165:Palladium; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry
D002712:Chlorides; D006841:Hydrocarbons, Aromatic; D013438:Sulfhydryl Compounds; D013440:Sulfides; D010165:Palladium