Alkyl-alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature

A commercially available 1,2-diamine serves as an effective ligand for metal-catalyzed cross-couplings of unactivated alkyl electrophiles at room temperature. In particular, Ni/trans-N,N'-dimethyl-1,2-cyclohexanediamine provides the first method for achieving alkyl-alkyl Suzuki reactions of unactivated secondary alkyl halides with alkylboranes; earlier success in Suzuki couplings of such electrophiles had been restricted to reactions with aryl- and vinylboron reagents at elevated temperature.