Base Catalysis Enables Access to α,α-Difluoroalkylthioethers.
Douglas L OrsiBrandon J EasleyAshley M LickRyan A AltmanPublished in: Organic letters (2017)
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.