Electrofluorination of Organic Compounds

Abstract

Methods for fluorinating org. compds. are described herein. The method comprises providing an org. compd., selected from organostannanes, organoboranes, or organosilanes, a silver-contg. compd., and a fluorinating agent under conditions sufficient to fluorinate the org. compd., thereby providing a fluorinated org. compd. Thus, 3-deoxy-3-(tributylstannyl)estrone (I; R = SnBu4) was treated sequentially with silver triflate in Et2O followed by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) and more silver triflate in acetone to give 85% 3-deoxy-3-fluoroestrone (I; R = F). [on SciFinder(R)]