Taming the captodative glycyl radical for nickel-photocatalytic cross-coupling with alkyl chlorides

Abstract

The captodatively stabilized glycyl radical was engaged in nickel photocatalysed C(sp³)–C(sp³) cross-coupling to obtain non-canonical amino acids. DFT-guided optimization of the amine protecting groups allowed for radical destabilization and tuning of its SOMO–LUMO gap. Optimization and control experiments highlight a radical cross-coupling mechanism.