Electrochemical Synthesis of Selenium‐substituted Benzoxazine via Radical Initiated Cyclization

Abstract

A strategy for electrochemically synthesizing selenium benzoxazines through o-vinylaniline and diselenide has been developed. This metal-free and oxidant-free electrochemical synthesis method is carried out in an undivided cell under mild conditions, which is more environmentally friendly. Moreover, a variety of selenium-substituted benzoxazine can be prepared in good yield with a broad scope and functional group tolerance, which has potential industrial application value.

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

“…In 2021, Fang and Hu et al also accomplished an electrochemical cyclization strategy to prepare selenium-substituted benzoxazines from o -vinylaniline and diselenide (Scheme 48). 63 When an aliphatic, naphthalene or thiophene is substituted for the benzene of olefin amide, the desired products can still be obtained in moderate to good yields. Whether it is dialkyl diselenides or diaryl diselenides, the desired product can also be obtained in good yields.…”

Recent progress in the electrochemical selenofunctionalization of alkenes and alkynes

“…94 For example, Hu, Fang and co-workers disclosed an electrochemical approach for synthesizing selenium benzoxazines from 2-vinylbenzamide and diselenide (Scheme 40). 95 An efficient reaction protocol was established after a series of reactions between N -(2-vinylphenyl) benzamides and diselenides using an undivided cell composed of a graphite rod anode and a Pt plate cathode. The expected seleno-substituted product was furnished in 95% yield when the reaction was performed in the presence of n Bu 4 NBF 4 as the supporting electrolyte and a constant current of 10 mA in CH 3 CN at room temperature.…”