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

Author:

Kong Xianqiang,Chen Xiaohui,Cao Zhong-Yan1,Chen Qisheng,Xiang Kai2,Chen Yiyi3

Affiliation:

1. College of Chemistry and Chemical Engineering, Henan University

2. Beijing Key Laboratory of Research and Application for Aerospace Green Propellants, Beijing Institute of Aerospace Testing Technology

3. School of Chemical Engineering and Materials, Changzhou University

Abstract

AbstractA 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.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Henan Province

China Three Gorges University

Publisher

Georg Thieme Verlag KG

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