Versatile electrooxidative amino- and oxyselenation of alkenes

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.

Automated summary

Here, we present a general and environmentally friendly electrochemical method for amino- and oxyselenation of alkenes without the use of transition-metal catalysts or additional oxidants. This electrocatalytic difunctionalization reaction demonstrates high chemoselectivity and can be applied to a wide range of substrates with various functional groups. We synthesized selenation products from diverse alkenes, including challenging 1-aryl-1,3-dienes, unactivated aliphatic alkenes, and N- or O-centered nucleophiles. Mechanistic studies were conducted and the practical utility of this approach was demonstrated through gram-scale synthesis and late-stage modification of bioactive molecules.