Generation and cross-coupling of benzyl and phthalimide-N-oxyl radicals in a cerium(IV) ammonium nitrate/N-hydroxyphthalimide/ArCH2R system

Generation and cross-coupling of benzyl and phthalimide-N-oxyl radicals in a cerium(IV) ammonium nitrate/N-hydroxyphthalimide/ArCH2R system Full article

Journal

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

Output data

Year: 2012, Volume: 68, Number: 50, Pages: 10263-10271 Pages count : 9 DOI: 10.1016/j.tet.2012.10.018

Authors

Terent'ev Alexander O. ¹ , Krylov Igor B. ¹ , Sharipov Mikhail Y. ¹ , Kazanskaya Zoya M. ¹ , Nikishin Gennady I. ¹

Affiliations

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

A method was developed for the cross-dehydrogenative coupling of alkylarenes and related compounds with N-hydroxyphthalimide (NHPI) using cerium(IV) ammonium nitrate (CAN) to prepare O-substituted NHPI derivatives. The characteristic feature of the reaction is that NHPI plays a dual role. Thus, in the presence of CAN, NHPI generates the phthalimide-N-oxyl (PINO) radical, which abstracts a hydrogen atom from the benzyl position to form a C-centered radical. The target oxidative cross-coupling product is formed mainly through the recombination of PINO with the C-centered radical. Therefore, NHPI serves as a mediator for the radical process and a reagent for the radical cross-coupling. The target products were obtained in yields from 35 to 80%.

Terent'ev A.O. , Krylov I.B. , Sharipov M.Y. , Kazanskaya Z.M. , Nikishin G.I.
Generation and cross-coupling of benzyl and phthalimide-N-oxyl radicals in a cerium(IV) ammonium nitrate/N-hydroxyphthalimide/ArCH2R system
Tetrahedron. 2012. V.68. N50. P.10263-10271. DOI: 10.1016/j.tet.2012.10.018 WOS Scopus OpenAlex

≡ Web of science:	WOS:000311135700001
≡ Scopus:	2-s2.0-84869089163
≡ OpenAlex:	W2950106836