1,2-Amino Alcohols via Visible-Light-Mediated Mannich-Type Reaction Enabled by Brook Rearrangement

Herein, we report a catalyst-free, photosensitized strategy for synthesizing 1,2-amino alcohols. This transformation proceeds via the addition of an α-hydroxymethyl radical to an in situ-generated alkyliminium ion. The α-hydroxymethyl radical is formed by the radical Brook rearrangement of a (trimethylsilyl)methoxy radical generated from an electron donor-acceptor (EDA) complex between Hantzsch ester and N-((trimethylsilyl)methoxy)phthalimide. Therefore, this Mannich-type reaction establishes an additive-free, modular, and simple approach for the synthesis of 1,2-amino alcohols.