Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide. Issue 17 (26th April 2019)

• Record Type: Journal Article
• Authors: Krylov, Igor B.; Paveliev, Stanislav A.; Matveeva, Olesya K.; Terent'ev, Alexander O.
• Is Part Of: Tetrahedron. Volume 75:Issue 17(2019)
• Page Start: 2529
• Page End: 2537
• Publication Date: 2019-04-26
• Subjects: Free radicals -- Imide-N-oxyl radicals -- N-hydroxyimides -- Oxidative functionalization -- Cerium(IV) ammonium nitrate; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.03.030
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Cerium(IV) ammonium nitrate was found to be a versatile reagent for the oxidative functionalization of styrenes using N -hydroxyphthalimide and iodine affording three different types of products with oxyphthalimide, nitrate and iodide groups. It was shown that reaction of styrenes with N -hydroxyphthalimide and cerium(IV) ammonium nitrate can be selectively directed to oxynitro-oxyphthalimides and dioxyphthalimides depending on the reaction conditions, in particular a solvent. Reaction of styrenes with iodine under the action of N -hydroxyphthalimide and cerium(IV) ammonium nitrate leads to the formation of iodo-oxyphthalimides. Graphical abstract: Image 1