Fluoro-lactonization of 4-alkenoic acid derivatives with N-fluoropentachloropyridinium triflate

Article abstract of DOI:10.1016/S0022-1139(96)03542-7

Fluoro-lactonization of 4-alkenoic acid derivatives containing an aryl substituent at the 4-or 5-position with N-fluoropentachloropyridinium triflate proceeds smoothly in a regioselective manner with little or no diastereoselectivity. These reactions possibly involve aryl-stabilized α-fluorocarbocation intermediates formed via single electron transfer from the pyridinium salt to the olefin as the first step.