Suzuki Cross-Couplings of Alkyl Tosylates that Possess β Hydrogen Atoms: Synthetic and Mechanistic Studies


  • We thank Johnson Matthey Inc. for supplying palladium compounds. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, R01-GM62871), the Natural Sciences and Engineering Research Council of Canada (postdoctoral fellowship to M.R.N.), and Novartis.


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A striking dependence of reactivity on phosphane structure was observed in the first Suzuki-type cross-coupling process that is effective for functionalized alkyl tosylates. In this reaction, in which solely commercially available reagents are used, PtBu2Me is the ligand of choice. Through the use of deuterium-labeled compounds, it has been established that the coupling proceeds with predominant inversion of configuration at the carbon atom [Eq. (1), 9-BBN=9-borabicyclo[3.3.1]nonane].