A General Platform for S ‐Stereogenic α‐Fluoroalkyl S(IV/VI) Compounds via Enantioselective Radical Fluoroalkylation of Sulfenamides

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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.
Funding Information
  • National Natural Science Foundation of China (22331006)
  • National Natural Science Foundation of China (22271133)
  • National Natural Science Foundation of China (22501127)

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