Water-Involved 1,3-Aminoxylation of Fluoroalkenes: Chemo-, Regio-, and Stereoselective Synthesis of β-Fluoroacyl Vinylamines

Abstract

Perfluoroalkyl alkenyl iodides (PFAIs) are emerging as highly reactive, storage-stable, and multifunctional fluoroalkyl-bearing reagents, facilitating the manufacture of value-added organofluorides through multi-halo-functionalization. Herein, we developed a water-involved 1,3-aminoxylation of PFAIs with sulfonamides for the chemo-, regio-, and Z-stereoselective synthesis of valuable β-fluoroacyl vinylamines. This reaction proceeded via a sequential deiodoamination and defluoroxylation process under transition-metal-free conditions, featuring a broad substrate scope and good functional group tolerance. Compared to reported methods, some drawbacks, such as multistep manipulation, harsh reaction conditions, the need for expensive catalysts, and the use of toxic/sensitive reagents, could be eliminated. Furthermore, the synthetic potential of this method was demonstrated through scale-up synthesis, postfunctionalization of complex molecules, and ready transformation of the products.