A Practical Electrochemical Approach for Synthesizing Selenyl-Dihydrobenzofurans and Chromane with a Tetrasubstituted Carbon Center

Synthesis Pub Date : 2024-06-24 DOI:10.1055/s-0043-1775373
Qisheng Chen, Kai Xiang, Yiyi Chen, Xianqiang Kong, Xiaohui Chen, Zhong-Yan Cao
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Abstract

A straightforward and efficient electrochemical method for the anodic oxidative selenenylation of 2-(2-arylallyl)phenols and a 2-(3-arylbut-3-en-1-yl)phenol with diselenides under ambient air conditions has been outlined. This method allows for the synthesis of selenyl-dihydrobenzofurans and a chromane featuring a sterically hindered tetrasubstituted carbon center, demonstrated through 25 examples with yields reaching up to 98%. Initial mechanistic investigations suggest the likely participation of pivotal seleniranium cation species in regulating the reactivity.

Abstract Image

合成硒基二氢苯并呋喃和以四取代碳为中心的铬烷的实用电化学方法
本研究概述了一种简单高效的电化学方法,用于在环境空气条件下用二硒化物对 2-(2-芳基烯丙基)苯酚和一种 2-(3-芳基丁-3-烯-1-基)苯酚进行阳极氧化硒化反应。这种方法可以合成硒基二氢苯并呋喃和一种以立体受阻的四取代碳中心为特征的色烷,通过 25 个实例进行了证明,收率高达 98%。初步的机理研究表明,关键的硒钛阳离子物种可能参与了反应活性的调节。
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