Photocatalytic Trifluoromethylimination and Sulfonylimination of N -Homoallylsulfonyl Hydrazones with Sulfonyl Chlorides Via Remote 1,4-Imine Migration
Abstract
A visible-light-mediated trifluoromethylimination and sulfonylimination of N-homoallylsulfonyl hydrazones has been developed via remote 1,4-imine migration using readily available sulfonyl chlorides as radical precursors. In the presence of 4CzIPN and 1,4-dioxane serving as both reaction medium and hydrogen atom transfer reagent, a variety of CF3-containing sulfonamide derivatives are efficiently synthesized. Switching the catalytic system to fac-Ir(ppy)3/NaOAc in THF enables the analogous sulfonylimination toward structurally diverse β-amino sulfones. A radical cascade pathway featuring alkene radical addition, N-N homolytic cleavage, β-scission-triggered 1,4-imine migration, and a HAT process was proposed.
Fields of Study & Subjects
Fluorine in Organic Chemistry
Sulfur-Based Synthesis Techniques
Radical Photochemical Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 30
- Pages
- 9684–9689
- Publication date
- 15 July 2026
- Language
- EN