Defluorinative functionalization of perfluoroalkyl alkenes with ureas: synthesis of C4-perfluoroalkenyl 2-imidazolones

Abstract

The C–F bond functionalization of polyfluoroalkyl substances has emerged as a significant research direction in the synthesis of organofluorides, owing to their unique chemical properties and potential synthetic applications. A defluorinative 1,2,3,4-tetrafunctionalization of perfluoroalkyl iodoalkenes with readily available ureas via multi-bond interconversion at four carbon sites has been developed. Taking advantage of the transformation of one C(sp²)–I, one C(sp²)–H, and two elusive C(sp³)–F bonds in a single reaction step, this transition-metal-free method provides facile access to a variety of perfluoroalkenyl 2-imidazolones. This protocol features a broad substrate scope, good functional group compatibility, moderate stereoselectivity, and mild reaction conditions.