Cerium(IV) ammonium nitrate promoted synthesis of O-phthalimide oximes from vinyl azides and N-hydroxyphthalimide

Cerium(IV) ammonium nitrate promoted synthesis of O-phthalimide oximes from vinyl azides and N-hydroxyphthalimide Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2020, Volume: 61, Number: 47, Article number : 152533, Pages count : DOI: 10.1016/j.tetlet.2020.152533

Authors

Paveliev Stanislav A. ¹ , Alimkhanova Liliya S. ^2,1 , Sergeeva Anna V. ^2,1 , Terent'ev Alexander O. ^2,1

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation

O-Phthalimide oximes with an Nsingle bondOsingle bondN fragment were synthesized in high yields via the reaction of vinyl azides with phthalimide-N-oxyl radicals derived from N-hydroxyphthalimide under the action of cerium(IV) ammonium nitrate. The disclosed process is based on the radical transformation of vinyl azides with the elimination of nitrogen and the formation of iminyl N-radicals. The developed approach exploited the dual reactivity of imide-N-oxyl radicals. They act as O-components for oxidative Csingle bondO coupling with vinyl azides and participate in subsequent formation of the Nsingle bondO bond via their recombination with intermediate iminyl radicals.

Paveliev S.A. , Alimkhanova L.S. , Sergeeva A.V. , Terent'ev A.O.
Cerium(IV) ammonium nitrate promoted synthesis of O-phthalimide oximes from vinyl azides and N-hydroxyphthalimide
Tetrahedron Letters. 2020. V.61. N47. 152533 . DOI: 10.1016/j.tetlet.2020.152533 WOS Scopus OpenAlex

Web of science:	WOS:000588310000004
Scopus:	2-s2.0-85092787223
OpenAlex:	W3091808945

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OpenAlex	10
Scopus	10
Web of science	9