Trifluoromethylated cyclopropanes and epoxides from CuI-mediated transformations of α-trifluoromethyl-diazophosphonate

An efficient method for the preparation of α-(trifluoromethyl)-cyclopropylphosphonates and α-(trifluoromethyl)-1,2-epoxyphosphonates has been developed. The method is based on metal-catalyzed reaction of diethyl 1-diazo-2,2,2-trifluoroethylphosphonate (1) with alkenes or carbonyl compounds, respectively. It established an essential advantage of CuI-catalysis over Rh2(OAc)4 in cyclopropanation reactions. An inexpensive copper iodide has also exhibited a good catalytic activity in the synthesis of epoxyphosphonates (3).

An efficient method for transformation of diethyl 1-diazo-2,2,2-trifluoroethylphosphonate to α-(trifluoromethyl)-cyclopropylphosphonates and α-(trifluoromethyl)-1,2-epoxyphosphonates has been developed. Figure optionsDownload as PowerPoint slide