Base Catalysis Enables Access to α,α-Difluoroalkylthioethers.
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.
Department of Medicinal Chemistry, The University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
Douglas L
0000-0001-6731-5494
DL
Orsi
Department of Medicinal Chemistry, The University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
Brandon J
BJ
Easley
Department of Medicinal Chemistry, The University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
Ashley M
AM
Lick
Department of Medicinal Chemistry, The University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
Ryan A
0000-0002-8724-1098
RA
Altman
D002384:Catalysis; D017611:Fluorine Compounds; D015394:Molecular Structure; D013440:Sulfides / Q000737:chemistry*
D017611:Fluorine Compounds; D013440:Sulfides