Photoinduced Smiles Rearrangement of N -Sulfonylpropargylamines for Highly Stereoselective Access to Tetrasubstituted Allylamines

Organic Letters 2026

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Authors: Tian-Shu Zhang, Wenchang Zhuang, Shu-Min Lu, Jia-Bao ZHU, Shuai Liu, Man‐Su Tu, Wen-Juan Hao, Bo Jiang
DOI: 10.1021/acs.orglett.6c00273
Cited by: 3
References: 59

Abstract

Smiles rearrangement enables the migration and structural reorganization of aromatic rings, providing an efficient strategy for the construction of tetrasubstituted alkenes. Despite significant advances, examples of Smiles rearrangements involving inert propargylamines remain limited owing to restricted substrate availability and inherent reactivity challenges. Herein, we report a photocatalyst-free photochemical radical Smiles rearrangement of N -sulfonylpropargylamines via 1,4-N-to-C aryl migration, affording valuable polysubstituted allylamines with high stereoselectivity. Notably, the resulting sulfur-containing tetrasubstituted allylamines exhibit pronounced aggregation-induced emission (AIE) properties, highlighting their potential in organic synthesis and advanced materials science.

Fields of Study & Subjects

Radical Photochemical Reactions Catalytic C–H Functionalization Methods Synthesis and Catalytic Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
10
Pages
3230–3235
Publication date
27 February 2026
Language
EN