Visible-light-mediated installation of unactivated alkyl groups enabling access to non-natural amino acid derivatives: detailed mechanistic insights

Abstract

Silane-mediated, visible-light-driven alkylation of electron-deficient olefins, enabling streamlined access to non-natural amino acid derivatives from unactivated halides, is reported here. Tris(trimethylsilyl)silane (TTMS) serves as both XAT and HAT reagents, enabling efficient radical generation and broad substrate scope including bioactive alkyl iodides. Comprehensive DFT investigations elucidate the reaction mechanism, delineating key intermediates and transition states.