Issue 10, 2023

Versatile electrooxidative amino- and oxyselenation of alkenes

Abstract

Herein, we describe a general and eco-friendly electrochemical methodology for amino- and oxyselenation of alkenes under transition-metal catalyst- and additional-oxidant-free conditions. This electrocatalytic difunctionalisation reaction exhibits excellent chemoselectivity, ample substrate scope, and high functional group tolerance. To our delight, the selenation products (118 examples, up to 99% yield) were constructed from various alkenes including the challenging 1-aryl-1,3-dienes, unactivated aliphatic alkenes, and various N- or O-centered nucleophiles. Preliminary mechanistic studies were conducted. The practical utility of this protocol is highlighted by the gram-scale synthesis and late-stage modification of bioactive molecules.

Graphical abstract: Versatile electrooxidative amino- and oxyselenation of alkenes

Supplementary files

Article information

Article type
Paper
Submitted
12 Mar 2023
Accepted
07 Apr 2023
First published
12 Apr 2023

Green Chem., 2023,25, 3925-3930

Versatile electrooxidative amino- and oxyselenation of alkenes

R. Wang, N. Zhang, Y. Zhang, B. Wang, Y. Xia, K. Sun, W. Jin, X. Li and C. Liu, Green Chem., 2023, 25, 3925 DOI: 10.1039/D3GC00837A

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