Ligands for Palladium-Catalyzed Cross-Couplings of Alkyl Halides: Use of an Alkyldiaminophosphane Expands the Scope of the Stille Reaction


  • We thank Johnson Matthey for supplying palladium compounds. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, R01-GM62871), Merck, and Novartis. Funding for the MIT Department of Chemistry Instrumentation Facility has been furnished in part by NSF CHE-9808061 and NSF DBI-9729592.


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Alkyldiaminophosphanes (PR(NR′2)2) are a new class of ligands for palladium-catalyzed cross-couplings of alkyl halides (see scheme). In comparison with trialkylphosphanes, alkyldiaminophosphanes furnish more versatile catalysts for Stille reactions of alkyl bromides and achieve efficient couplings with both vinyl and aryl stannanes. Furthermore, Pd/PR(NR′2)2 provides the first method for accomplishing Stille cross-couplings of simple alkyl iodides that bear β-hydrogen atoms.