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

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.

Key words

oxyselenenylation - electrosynthesis - tetrasubstituted carbon center - dihydrobenzofurans - chromane

Publication History

Received: 02 May 2024

Accepted after revision: 04 June 2024

Article published online:
24 June 2024

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