Electrifying Phthalimide-N-Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with N-Hydroxyphthalimide

Electrifying Phthalimide-N-Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with N-Hydroxyphthalimide Full article

Journal

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

Output data

Year: 2021, Volume: 86, Number: 24, Pages: 18107-18116 Pages count : 10 DOI: 10.1021/acs.joc.1c02367

Authors

Paveliev Stanislav A. ¹ , Segida Oleg O. ¹ , Dvoretskiy Andrey ² , Dzyunov Mark M. ³ , Fedorova Uliana V. ² , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation
3	Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, Moscow 119991, Russian Federation

An electrochemical process of free-radical difunctionalization of vinyl arenes with N-hydroxyphthalimide resulting in vicinal dioxyphthalimides was discovered. The reaction proceeds with the use of pyridinium perchlorate and pyridine as a supporting electrolyte and a base, respectively. The present approach involves the anodic generation of stabilized phthalimide-N-oxyl (PINO) radical, which adds to the carbon–carbon double bond of vinyl arenes and recombines with the subsequently formed benzylic radical. A wide range of dioxyphthalimides were obtained in yields up to 81%.

Paveliev S.A. , Segida O.O. , Dvoretskiy A. , Dzyunov M.M. , Fedorova U.V. , Terent’ev A.O.
Electrifying Phthalimide-N-Oxyl (PINO) Radical Chemistry: Anodically Induced Dioxygenation of Vinyl Arenes with N-Hydroxyphthalimide
Journal of Organic Chemistry. 2021. V.86. N24. P.18107-18116. DOI: 10.1021/acs.joc.1c02367 WOS Scopus OpenAlex

≡ Web of science:	WOS:000730353300001
≡ Scopus:	2-s2.0-85121035975
≡ OpenAlex:	W4200508382