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

Organic Letters 2026

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Authors: Ai-Lian Wang, Yifan Yao, Xu-Gang Zhang, Peng-Fei Xu
DOI: 10.1021/acs.orglett.5c04773
Cited by: 4
References: 52

Abstract

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.

Fields of Study & Subjects

Radical Photochemical Reactions Catalytic C–H Functionalization Methods Oxidative Organic Chemistry Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
5
Pages
1550–1556
Publication date
26 January 2026
Language
EN