A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.
A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of 1 occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.
Department of Chemistry, Yale University, PO Box 208107 New Haven, CT 06520-8107, USA.
Manuel A
MA
Fernández-Rodríguez
Qilong
Q
Shen
John F
JF
Hartwig
D000840:Anisoles / Q000737:chemistry; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D009795:Octanes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D000840:Anisoles; D006846:Hydrocarbons, Halogenated; D009795:Octanes; D013438:Sulfhydryl Compounds; D013440:Sulfides; D010165:Palladium