Hydroxyalkylation of α-Silylamines via a Photoredox Polarity-Matched Strategy

A step-economic, photoredox-catalyzed hydroxyalkylation of nucleophilic α-silylamines with diverse electrophilic carbonyls to access biologically relevant β-amino alcohols. In contrast to the classical multistep Henry reaction, this one-step approach utilizes a polarity-matched strategy to directly forge the target scaffolds. This protocol features remarkable substrate/functional group compatibility, scale-up potential, and facile late-stage modification. Mechanistic studies reveal the formation of the α-amino radical from α-silylamines by a single-electron oxidative desilylation.