Analysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions

The use of tpy' (tpy' = 4,4',4-tri-tert-butyl-terpyridine) as a ligand for nickel allows for the isolation of a Ni(I)-alkyl complex and a Ni(II)-alkyl halide complex, both of which can be used as mechanistic probes of key steps in alkyl cross-coupling reactions.