Photosensitizer-free polarity-mismatched electrophilic α,α-bis-functionalization of acetone with quinoxaline and maleimide

Abstract

A polarity-mismatch-driven, photosensitizer-free protocol for the α,α-bis-functionalization of acetone has been developed, employing quinoxaline and maleimide as coupling partners. The photoactive species is identified as the ion-pair complex of protonated 2-phenylquinoxaline with methanesulfonate, wherein photoinduced electron transfer (PET) serves as the key mechanistic pathway. To the best of our knowledge, this is a unique photo-induced α,α-bisfunctionalization of acetone.