Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 24, Pages 18107-18116Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02367
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- Russian Science Foundation [21-13-00205]
- Russian Science Foundation [21-13-00205] Funding Source: Russian Science Foundation
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A novel electrochemical process was developed for the difunctionalization of vinyl arenes with N-hydroxyphthalimide, resulting in vicinal dioxyphthalimides. The reaction involves the anodic generation of stabilized phthalimide-N-oxyl radical, which adds to the carbon-carbon double bond of vinyl arenes and recombines with the subsequently formed benzylic radical to afford a wide range of dioxyphthalimides with yields up to 81%.
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%.
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