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

Abstract

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].