Transition-metal-free defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles: Synthesis of (E)-perfluoroalkenyl pyrroles

Functionalization of the C-F bond in perfluoroalkyl substances represents an emerging focus in organic chemistry. We report here a transition-metal-free intermolecular defluorinative cyclization of perfluoroalkyl alkenyl iodides with C,N-dinucleophiles. This method enables highly chemo-, regio-, and stereoselective 2-fold C(sp 3 )-F bond cleavage at two vicinal carbon centers in the perfluoroalkyl chain, resulting in the assembly of a five-membered N-heterocycle with a structurally privileged (E)-prefluoroalkenyl unit. The success of partial defluorination is mainly attributed to the pre-installed alkenyl functionality and iodide atom in perfluoroalkyl substances. A transition-metal-free intermolecular defluorinative cyclization of perfluoroalkyl alkenyl iodides with C , N -dinucleophiles for the synthesis of ( E )-perfluoroalkenyl pyrroles has been developed.