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Updated: Jun 16, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
N-Sulfinyl Phthalimides as Modular Sulfinyl Radical Precursors: PRE-Guided Chemoselective Alkene Difunctionalization
Changmei Zhang1, Yuxuan He1, Heping Tan1
1State Key Laboratory of Materials-Oriented Chemical Engineering, College of ChemicalEngineering, Nanjing Tech University, South Puzhu Road 30, Nanjing211816, China.
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Despite the importance of sulfoxides in synthesis and biology, the utilization of sulfinyl radicals for their construction remains underexplored compared to other sulfur-centered radicals. While the Persistent Radical Effect (PRE) offers a powerful framework to harness these stabilized species for radical-radical cross-coupling, the development of general transformations is rare due to the lack of modular sulfinyl radical precursors. Herein, we report N-sulfinyl phthalimides as bench-stable, modular precursors that selectively liberate persistent sulfinyl radicals upon single-electron reduction. This strategy enables the first general 1,2-trifluoromethyl-sulfinylation of unactivated alkenes and robust PRE-guided cross-couplings with diverse alkyl radicals derived from C-H bonds, Hantzsch esters, or carboxylic acids. Furthermore, we report the first generation of unsymmetrical sulfinyl sulfones and elucidate a mechanism driven by their rapid tautomerization, enabling a catalyst-free, ambient-temperature protocol for the direct conversion of sulfinate salts into sulfoxides. The broad utility of these protocols is demonstrated by the successful difunctionalization of ethylene gas and the late-stage modification of complex medicinal compounds, alongside versatile product derivatizations. This work establishes a versatile platform for radical sulfinylation governed by precise kinetic control.
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