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  • Title: A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.
    Author: Fernández-Rodríguez MA, Shen Q, Hartwig JF.
    Journal: J Am Chem Soc; 2006 Feb 22; 128(7):2180-1. PubMed ID: 16478149.
    Abstract:
    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.
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