Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide

Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2019, Volume: 75, Number: 17, Pages: 2529-2537 Pages count : 9 DOI: 10.1016/j.tet.2019.03.030

Authors

Krylov Igor B. ^1,2 , Paveliev Stanislav A. ¹ , Matveeva Olesya K. ^3,1 , Terent'ev Alexander O. ^1,3,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prosp., Moscow, 119991, Russian Federation
2	All-Russian Research Institute for Phytopathology, B. Vyazyomy, Moscow Region, 143050, Russian Federation
3	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow, 125047, Russian Federation

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.

Krylov I.B. , Paveliev S.A. , Matveeva O.K. , Terent'ev A.O.
Cerium(IV) ammonium nitrate: Reagent for the versatile oxidative functionalization of styrenes using N-hydroxyphthalimide
Tetrahedron. 2019. V.75. N17. P.2529-2537. DOI: 10.1016/j.tet.2019.03.030 WOS Scopus OpenAlex

≡ Web of science:	WOS:000465052300009
≡ Scopus:	2-s2.0-85063281374
≡ OpenAlex:	W2924720437