Electrochemically Induced Synthesis of N-Allyloxyphthalimides via Cross-Dehydrogenative C–O Coupling of N-Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom

Electrochemically Induced Synthesis of N-Allyloxyphthalimides via Cross-Dehydrogenative C–O Coupling of N-Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom Full article

Journal

ACS omega
ISSN: 2470-1343

Output data

Year: 2024, Volume: 9, Number: 50, Pages: 49825–49831 Pages count : DOI: 10.1021/acsomega.4c08532

Authors

Paveliev Stanislav A. ¹ , Segida Oleg O. ¹ , Dvoretskiy Andrey 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

The electrochemically induced reaction between alkenes, bearing an allylic hydrogen atom, and N-hydroxyphthalimide was investigated. Cross-dehydrogenative C–O coupling with phthalimide-N-oxyl radical, derived from N-hydroxyphthalimide, occurs instead of oxidation of the allylic site, with the formation of a carbonyl group or functionalization of the double C═C bond. The discovered transformation proceeds in an undivided electrochemical cell equipped with a carbon felt anode and a platinum cathode. Coupling products were obtained with yields up to 79%. The developed process is based on the abstraction of hydrogen atom from the allylic position for functionalization while the C═C bond remains unreacted. The method exploits the ability of the phthalimide-N-oxyl radical to abstract hydrogen atoms with the following interception of the intermediate C-centered radical.

Paveliev S.A. , Segida O.O. , Dvoretskiy A. , Terent’ev A.O.
Electrochemically Induced Synthesis of N-Allyloxyphthalimides via Cross-Dehydrogenative C–O Coupling of N-Hydroxyphthalimide with Alkenes Bearing the Allylic Hydrogen Atom
ACS omega. 2024. V.9. N50. P.49825–49831. DOI: 10.1021/acsomega.4c08532 WOS OpenAlex

Web of science:	WOS:001368381800001
OpenAlex:	W4404922753

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