Selectfluor and Alcohol Mediated Synthesis of Bicyclic Oxyfluorination Compounds by Wagner-Meerwein Rearrangement

Abstract

Herein, we report the first environmentally friendly systematic fluoroalkoxylation reactions in bicyclic systems. New oxyfluorination products were obtained with excellent yields (up to 99%) via Wagner-Meerwein rearrangement using benzonorbornadiene and chiral natural compound (4)-camphene as bicyclic alkenes, selectfluor as an electrophilic fluorine source, and water and various alcohols as nucleophile sources. The structure of bicyclic oxy- and alkoxyfluorine compounds was determined by NMR and GC-MS analyses.