Nickel catalyzed cross-coupling of modified alkyl and alkenyl Grignard reagents with aryl- and heteroaryl nitriles: activation of the CCN bond

Abstract

The nickel catalyzed cross-coupling of alkyl and alkenyl Grignard reagents with aryl nitrile derivatives affords good yields of the corresponding aryl alkanes or aryl alkenes via activation of the CCN bond. To prevent direct addition of the nucleophile to the nitrile group, the reactivity of the Grignard reagent was modulated by reaction with either LiO t-Bu or PhSLi prior to cross-coupling. The optimum catalyst was determined to be NiCl 2(PMe 3) 2, which is a convenient air stable commercially available complex.