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Updated: May 13, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Visible-Light-Promoted C(sp2)-Monofluoromethylation and Difunctionalization of Alkenes with Bench-Stable Sulfonyl
Mamtimin Ablajan1, Xin Fu1, Xi-Sheng Wang2
1Department of Chemistry, Xinjiang Normal University, Urumqi 830054, China.
Abstract:
An efficacious and straightforward synthetic protocol for the incorporation of biologically and pharmaceutically prominent monofluoromethyl moiety onto alkenes with bench-stable and easily accessible sulfonyl monofluoromethyl iodides has been disclosed. By precise modulation of base, this methodology selectively facilitates two distinct pathways: radical-mediated Heck-type C(sp2)-H functionalization for the synthesis of allylic monofluoromethyl compounds, or alkene difunctionalization via sequential monofluoromethylation and iodination. The proposed mechanism was validated through mechanistic studies and density functional theory (DFT) calculations. The transformation is applicable to both activated and unactivated alkenes and exhibits operational simplicity, a broad substrate scope, and high atom economy.
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