A novel fluorine-metal exchange reaction of pentafluorocrotonate with organocuprate. Generation of beta-metallated tetrafluorocrotonate and its cross-coupling reaction

Chem Commun (Camb). 2007 Sep 21:(35):3679-81. doi: 10.1039/b705408d. Epub 2007 Jul 2.

Abstract

Fluorine-metal exchange reaction of 2,3,4,4,4-pentafluorocrotonates with organocuprate derived from Grignard reagent and CuCN takes place efficiently to generate the beta-metallated tetrafluorocrotonate intermediate, which reacts with various electrophiles to give beta-substituted 2,4,4,4-tetrafluorocrotonates.