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.