Ligandless Pentafluoroethylation of Unactivated (Hetero)aryl and Alkenyl Halides Enabled by the Controlled Self-Condensation of TMSCF3-Derived CuCF3

Identifier:  imarina:6012542

Handle: https://hdl.handle.net/20.500.11797/imarina6012542

Authors:  Mestre, J; Castillón, S; Boutureira, O

Abstract:
Pentafluoroethylation of unactivated C(sp(2))-X bonds (X = I, Br) using a storable, ligandless CuC2F5 reagent prepared by controlled self-condensation of ready available TMSCF3-derived CuCF3 has been developed. A thorough analysis by F-19 NMR and ESI-MS revealed the nature of this reagent in solution. The operational simplicity and robustness of this system enables the efficient, late-stage incorporation of C2F5 units into a variety of (hetero)aryl and complex alkenyl halides such as glycals, nucleosides, and nucleobases.