Silver-Promoted Three-Component Synthesis of Perfluoroalkenyl Pyrroles through Partial Defluorinative Functionalization of Perfluoroalkyl Halides

Abstract

A silver-promoted three-component heterocyclization of alkynes, perfluoroalkyl halides, and 1,3-dinucleophiles was developed for the efficient synthesis of privileged (E)-perfluoroalkenyl pyrroles. The reaction proceeded through a rationally designed sequence of radical perfluoroalkylation and intramolecular defluorinative [3 + 2]-heterocyclization. The utility of perfluoroalkyl halide as a perfluoroalkenyl reagent, by selective and controllable functionalization of two inert C(sp 3 )−F bonds at vicinal carbon centers on the perfluoroalkyl chain, provides a new reaction mode for the synthesis of value-added organofluorides starting from the easily available and low-cost fluorinated feedstock.Letter pubs.acs.org/OrgLett

Palladium-Catalyzed Regioselective Monofluoroallylation of Indoles with gem-Difluorocyclopropanes

“…Representative examples containing the fluorinated vinyl moiety are listed in Figure , including an atorvastatin analogue, a human parathyroid hormone analogue, a histone deacetylase inhibitor, and fluorinated resveratrol . As a result, the development of methods for the construction of vinyl fluorides has received much attention and numerous reactions have been reported over the past few decades . The condensation of aldehydes with organofluorine reagents and the hydrofluorination of alkynes are two types of general methodologies for their synthesis.…”