K. Dawood, S. Higashiya, Yankun Hou
Sep 28, 1999
Citations
0
Influential Citations
24
Citations
Journal
Journal of Organic Chemistry
Abstract
Highly regioselective electrochemical fluorination of 2-pyrimidyl sulfides having an electron-withdrawing group (EWG) at the position α to the sulfur atom was successfully carried out using Et4NF·nHF (n = 3, 4) or Et3N·3HF as a supporting electrolyte and a fluoride ion source in 1,2-dimethoxyethane (DME) in an undivided cell. 2-Methylthiopyrimidine devoid of an EWG was also selectively fluorinated in DME to provide 2-(fluoromethylthio)pyrimidine in a moderate yield as 63%, while corresponding 2-methylthiopyridine was less selectively fluorinated in lower yield along with α,α-difluorinated product. In contrast, the corresponding 2-quinazolinonyl sulfides underwent similarly α-fluorination along with unexpected ipso-fluorination through anodic desulfurization.