Visible light photoredox alkylazidation of alkenes with sodium azide and heteroarenium salts: entry to azido-containing 1,4-dihydropyridines

Chemical Communications : Chem Comm
Yuan YangJin-Heng Li

Abstract

A three-component alkene alkylazidation using sodium azide as the azido resource and heteroarenium salts as functionalized alkyl reagents for producing highly valuable 2-azido-1-(1,4-dihydropyridin-4-yl)-ethanes is described. This reaction allows the incorporation of both an azido group and a 1,4-dihydropyridin-4-yl group across C[double bond, length as m-dash]C bonds to construct two new bonds in a single reaction step, and represents a practical and mechanistically distinct alternative that harnesses an electrophilic heteroarenium ion to accomplish the alkene difunctionalization reaction.

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Citations

Nov 11, 2021·Organic Letters·Kaikai WangHongli Bao

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