25. Base Catalysis Enables Access to α,α-Difluoroalkylthio-ethers

Fluorinated AlkenesOrganofluorine MethodologySynthetic Organic MethodologyPre 2020
Written By Altmaniacs
 
 

Orsi, D. L.; Easley, B. J.; Lick, A. M.; Altman, R. A.*

Org. Lett. 2017, 19, 1570–1573.

A nucleophilic addition reaction of aryl thiols to readily available β,β-difluorostyrenes provides α,α-difluoroalkylthioethers. The reaction proceeds through an unstable anionic intermediate, prone to eliminate fluoride and generate α-fluorovinylthioethers. However, the use of base catalysis overcomes the facile β-fluoride elimination, generating α,α-difluoroalkylthioethers in excellent yields and selectivities.

Altmaniacs
Previous

26. Exploiting the Unusual Effects of Fluorine in Methodology
Next

24. Synthesis and Opioid Activity of Tyr1–ψ[(Z)CF=CH]–Gly2 and Tyr1–ψ[(S)/(R)-CF3CH–NH]–Gly2 Leu-enkephalin Fluorinated Peptidomimetics