Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

Abstract

A synthetic route to the bench-stable fluorinated masked carbene reagent diethyl 2-diazo-1,1,3,3,3-pentafluoropropylphosphonate, bearing a trifluoromethyl and a difluoromethyl group is reported for the first time. Its application in CuI-catalyzed cyclopropanation reactions with aromatic and aliphatic terminal alkenes under mild reaction conditions is demonstrated. In total, sixteen new cyclopropanes were synthesized in good to very good yields.

Keywords

• alkenes
• cyclopropanation
• diazo compounds
• difluoromethylphosphonate
• dft calculations