Oxidative addition of an alkyl halide to form a stable Cu(III) product.

ABSTRACT: The step that cleaves the carbon-halogen bond in copper-catalyzed cross-coupling reactions remains ill defined because of the multiple redox manifolds available to copper and the instability of the high-valent copper product formed. We report the oxidative addition of α-haloacetonitrile to ionic and neutral copper(I) complexes to form previously elusive but here fully characterized copper(III) complexes. The stability of these complexes stems from the strong Cu-CF₃ bond and the high barrier for C(CF₃)-C(CH₂CN) bond-forming reductive elimination. The mechanistic studies we performed suggest that oxidative addition to ionic and neutral copper(I) complexes proceeds by means of two different pathways: an S_N2-type substitution to the ion

SUBMITTER: Luo Y 

PROVIDER: S-EPMC10658983 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature