Organofluorine compounds are becoming increasingly important in different fields, such as material science,agro chemistry, and the pharmaceutical industry. Nucleophilic trifluoromethylation is one of the widelyused methods to incorporate a trifluoromethyl moiety into organic molecules. We have carried out extensivestudies to develop varieties of easily accessible nucleophilic catalysts to promote such reactions. TMS-protected trifluoromethylated alcohols were prepared from both aldehydes and ketones in excellent yieldsusing catalytic amount of amine
N-oxide. Carbonate and phosphate salts also showed efficient catalyticactivity toward this reaction. These reactions were highly solvent dependent, and DMF was found to bethe most suitable one among the various solvents studied. All these reactions proceeded under very mildconditions, giving clean products and avoiding the use of any fluoride initiators or expensive catalysts,and extremely water-free conditions. The mechanism for the reaction is discussed in detail. DFTcalculations were performed on the possible reaction intermediates using the Gaussian 03 program atB3LYP/6-311+G* level to support the proposed mechanism.
