Stereoselective Access to Trifunctionalized Z-Allylic Alcohols via Radical-Mediated 1,4-Aryl Migration
Xu Zhang1, Tao Niu2, Fushan Chen1
1Frontiers Science Center For Transformative Molecules, School of Chemistry and Chemical Engineering, and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai, China.
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Given the synthetic significance of allylic alcohols, developing efficient methods for their preparation remains a central pursuit in organic chemistry. Herein, we report a stereoselective approach to access trifunctionalized Z‑allylic alcohols via a radical‑mediated 1,4‑aryl migration. By employing readily available benzyl propargyl ethers and Togni-II reagent as the CF3 source, this reaction proceeds through inert C(sp2)-C(sp3) bond cleavage, enabling the modular assembly of valuable trifluoromethylated Z‑allylic alcohols under mild, photoredox‑neutral conditions. The protocol exhibits a broad substrate scope, excellent functional‑group tolerance, and high regio- and stereo-selectivity.
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