Tributyl(3,3,3-trifluoro-1-propynyl)stannane as an efficient reagent for the preparation of various trifluoromethylated heterocyclic compounds

Tributyl(3,3,3-trifluoro-1-propynyl)stannane was readily synthesized from 2-bromo-3,3,3-trifluoropropene in one step. The 1,3-dipolar cycloaddition of the stannane with diazomethane, phenylazide, and acetonitrile oxide smoothly proceeded to give the corresponding (tributylstannyl)trifluoromethyl-pyrazole, -triazole, and -isoxazole in good yields, respectively. These heterocyclic compounds are proved to be useful building blocks for the regioselective introduction of a functional group such as an aryl group or iodine.