Denitrogenative N–O Coupling of Benzyl Azides with N -Hydroxyphthalimide Mediated by Cerium(IV) Ammonium Nitrate as an Oxidant

Denitrogenative N–O Coupling of Benzyl Azides with N -Hydroxyphthalimide Mediated by Cerium(IV) Ammonium Nitrate as an Oxidant Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2026, Volume: 91, Number: 14, Pages: 4997-5005 Pages count : 9 DOI: 10.1021/acs.joc.5c03145

Authors

Paveliev Stanislav A. ¹ , Dvoretskiy Andrey A. ¹ , Segida Oleg O. ¹ , Krylov Igor B. ¹ , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russian Federation

An intermolecular N–O coupling process between iminyl radicals derived from benzyl azides and phthalimide-N-oxyl radicals, leading to the O-phthalimide oximes with a rare N–O–N fragment, was discovered. The present work reveals an unusual reactivity of organic azides: they are introduced into the denitrogenative generation of N-centered iminyl radicals via hydrogen atom abstraction from the α-position of the azide group. Moreover, the method exploits the dual reactivity of the phthalimide-N-oxyl radical, which acts both as a mediator of hydrogen atom abstraction and an interceptor of intermediate iminyl radicals.

Paveliev S.A. , Dvoretskiy A.A. , Segida O.O. , Krylov I.B. , Terent’ev A.O.
Denitrogenative N–O Coupling of Benzyl Azides with N -Hydroxyphthalimide Mediated by Cerium(IV) Ammonium Nitrate as an Oxidant
Journal of Organic Chemistry. 2026. V.91. N14. P.4997-5005. DOI: 10.1021/acs.joc.5c03145 WOS Scopus OpenAlex

Submitted:	Dec 15, 2025
Published online:	Mar 30, 2026

≡ Web of science:	WOS:001729100600001
≡ Scopus:	2-s2.0-105035863787
≡ OpenAlex:	W7143389423