Photoredox-catalyzed Giese reaction for the synthesis of γ-nitro alcohols

Abstract

The direct synthesis of γ-nitro alcohols, valuable precursors to 1,3-amino alcohols, from simple starting materials remains a challenge. Herein, we disclose a photoredox-catalyzed Giese reaction between (trimethylsilyl)methanol and nitroalkenes, operating under mild conditions to conveniently access a diverse array of γ-nitro alcohols. The synthetic utility of this protocol is demonstrated through its scalability and facile downstream conversion to valuable 1,3-amino alcohols. Mechanistic studies reveal that the reaction proceeds via a photoinduced radical Brook rearrangement followed by a Giese addition.