A General Platform for S-Stereogenic α-Fluoroalkyl S(IV/VI) Compounds via Enantioselective Radical Fluoroalkylation of Sulfenamides
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Updated: Jun 14, 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
Yu-Shuai Zhang1, Li-Wen Fan1, Pei-Jie Huang1
1New Cornerstone Science Laboratory, Shenzhen Grubbs Institute, Department of Chemistry, and Guangming Advanced Research Institute, Southern University of Science and Technology, Shenzhen, China.
Abstract:
α-Fluoroalkyl-substituted high-valent sulfur motifs are important structural elements in fluorinated molecule design and exhibit broad application potential in diverse fields. However, access to S-stereogenic α-fluoroalkyl S(IV/VI) compounds still relies largely on classical resolution, resulting in limited efficiency and selectivity. We herein report a copper-catalyzed asymmetric radical C-S cross-coupling that effectively tames highly reactive α-fluoroalkyl radicals, enabled by a sequential stereodiscrimination-chirality transfer strategy, providing rapid access to S-chiral α-fluoroalkyl sulfilimines. Integrated with downstream transformations, this reaction serves as a general and systematic platform for S-chiral α-fluoroalkyl S(IV/VI) compounds. The synthetic utility of the method is demonstrated by gram-scale synthesis and concise access to diverse chiral fluoroalkyl reagents and bioisosteres of sulfur-containing drugs.
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