Copper Catalyzed C(sp³)-H Bond Alkylation via Photoinduced Ligand-to-Metal Charge Transfer.

ABSTRACT: Utilizing catalytic CuCl₂ we report the functionalization of numerous feedstock chemicals via the coupling of unactivated C(sp³)-H bonds with electron-deficient olefins. The active cuprate catalyst undergoes Ligand-to-Metal Charge Transfer (LMCT) to enable the generation of a chlorine radical which acts as a powerful hydrogen atom transfer reagent capable of abstracting strong electron-rich C(sp³)-H bonds. Of note is that the chlorocuprate catalyst is an exceedingly mild oxidant (0.5 V vs SCE) and that a proposed protodemetalation mechanism offers a broad scope of electron-deficient olefins, offering high diastereoselectivity in the case of endocyclic alkenes. The coupling of chlorine radical generation with Cu reduction through LMCT enables the generation

SUBMITTER: Treacy SM 

PROVIDER: S-EPMC8608032 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature