The Journal of Organic Chemistry· 2026Q2
Stereoselective Defluorinative Thiolation of gem -Difluoroalkenes with Thiols via Nucleophilic Substitution
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- Q2SCImago
- 2026year
Short summary
A new transition-metal-free method stereoselectively converts gem-difluoroalkenes into monofluoroalkenyl sulfides using thiols and a base, achieving Z/E ratios up to 24:1.
AI-generated from the title and abstract; the full text is not read.
Key points
- Developed a transition-metal-free defluorinative thiolation of gem-difluoroalkenes.
- Reaction proceeds via nucleophilic substitution with base promotion.
- Achieves excellent stereoselectivity (Z/E up to 24:1) and good yields.
- Demonstrates broad substrate scope and functional group tolerance.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Monofluoroalkenes are valuable mimics of enol and amide bonds, making them important structural motifs in drug discovery. Herein, we report a transition-metal-free, stereoselective defluorinative thiolation of gem-difluoroalkenes with thiols under simple base promotion. This transformation proceeds efficiently through a nucleophilic substitution pathway, affording a broad array of monofluoroalkenyl sulfides in generally good yields with excellent stereoselectivities (Z/E up to 24:1). This protocol features a broad substrate scope and excellent functional group tolerance, representing a convenient approach to stereodefined monofluoroalkenyl sulfides.
The authors' abstract, as published at the source. The Journal of Organic Chemistry, 2026 · DOI ↗
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Field: Pharmaceutical Science
Pharmaceutical SciencePharmacology, Toxicology and Pharmaceutics