Department of Medicinal Chemistry, The University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
Org Lett. 2017 Apr 7;19(7):1570-1573. doi: 10.1021/acs.orglett.7b00386. Epub 2017 Mar 23.
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.
芳基硫醇对易得的β,β-二氟苯乙烯的亲核加成反应提供了α,α-二氟烷硫醚。该反应通过不稳定的阴离子中间体进行，容易消除氟并生成α-氟代乙烯基硫醚。然而，使用碱催化克服了易发生的β-氟消除，以优异的收率和选择性生成α,α-二氟烷硫醚。
