Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene

Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene Full article

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2022, Volume: 32, Number: 2, Pages: 167-169 Pages count : 3 DOI: 10.1016/j.mencom.2022.03.004

Authors

Paveliev Stanislav A. ¹ , Segida Oleg O. ¹ , Fedorova Uliana V. ² , Mulina Olga M. ¹ , Terent'ev Alexander O. ^2,1

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 125047 Moscow, Russian Federation

O,O′-Bis(phthalimido)-modified 2-(hydroxyimino)ethanols containing N–O–N fragment were synthesized in high yields via the reaction of vinyl azides with N-hydroxyphthalimide under the action of hypervalent iodine-based oxidant. The reaction proceeds under mild conditions and is compatible with a wide range of vinyl azides. Presumably, the process starts with the oxidative formation of phthalimide-N-oxyl radical, followed by its addition to vinyl azide with the subsequent trapping of the generated iminyl radical with the second phthalimide-N-oxyl radical.

Paveliev S.A. , Segida O.O. , Fedorova U.V. , Mulina O.M. , Terent'ev A.O.
Radical oxyamination of vinyl azides with N-hydroxyphthalimide under the action of [bis(trifluoroacetoxy)iodo]benzene
Mendeleev Communications. 2022. V.32. N2. P.167-169. DOI: 10.1016/j.mencom.2022.03.004 WOS Scopus OpenAlex

Web of science:	WOS:000807715400005
Scopus:	2-s2.0-85127336426
OpenAlex:	W4220895990

DB	Citing
OpenAlex	4
Scopus	5
Web of science	4