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 protection groups allowed for radical destabilization and tuning of its SOMO-LUMO gap. Optimization and control experiments highlight a radical cross-coupling mechanism.