From C₁ to C₂: TMSCF₃ as a Precursor for Pentafluoroethylation

Abstract

A highly efficient copper-mediated aromatic pentafluoroethylation method using TMSCF₃ as the sole fluoroalkyl source is described. The reaction proceeds by a key C₁ to C₂ process, that is, the generation of CuCF₃ from TMSCF₃ , followed by a subsequent spontaneous transformation into CuC₂ F₅ . Various aryl iodides were pentafluoroethylated with the TMSCF₃ -derived CuC₂ F₅ . This method represents the first practical and efficient method for pentafluoroethylation of aryl iodides using commercially available TMSCF₃ as a pentafluoroethyl precursor.