Paveliev Stanislav A, Segida Oleg O, Dvoretskiy Andrey, Dzyunov Mark M, Fedorova Uliana V, Terent'ev Alexander O
N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991, Russian Federation.
D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, Moscow 125047, Russian Federation.
J Org Chem. 2021 Dec 17;86(24):18107-18116. doi: 10.1021/acs.joc.1c02367. Epub 2021 Dec 8.
An electrochemical process of free-radical difunctionalization of vinyl arenes with -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--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%.
发现了一种电化学过程，即乙烯基芳烃与邻羟基苯二甲酰亚胺发生自由基双官能化反应生成邻二氧基苯二甲酰亚胺。该反应分别使用高氯酸吡啶和吡啶作为支持电解质和碱来进行。目前的方法涉及阳极生成稳定的邻苯二甲酰亚胺-氧自由基（PINO），其加成到乙烯基芳烃的碳-碳双键上，并与随后形成的苄基自由基重组。以高达81%的产率获得了多种二氧基苯二甲酰亚胺。
