Visible-light-driven dehalogenative oximation of alkyl halides

Abstract

A visible-light-driven, transition-metal-free dehalogenative oximation of simple alkyl halides has been developed, exploiting a boryl radical-mediated halogen atom transfer (XAT) process. This strategy efficiently converts readily available alkyl halides into diverse oximes under mild conditions. Gram-scale synthesis, diverse derivatization of the oxime products, and a concise route to Tioxazafen collectively highlight the strategy’s broad synthetic utility. The Z/E selectivity in the synthesis of aryl oximes can be controlled by the addition or omission of a triplet photosensitizer. Therefore, this protocol offers a practical paradigm for the diversified transformation of simple alkyl halides under transition metal-free conditions.