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KOBut/DMSO-Mediated α‑C–H Vinylation of N‑Benzyl Ketimines with Acetylene Gas: Stereoselective Synthesis of (E,Z)‑2-Azadienes

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journal contribution
posted on 25.03.2020, 11:37 by Ivan A. Bidusenko, Elena Yu. Schmidt, Nadezhda I. Protsuk, Igor A. Ushakov, Alexander V. Vashchenko, Andrei V. Afonin, Boris A. Trofimov
Several imines, readily derived from aryl methyl ketones and benzylamines, react with acetylene gas in KOBut/DMSO system to afford 2-azadienes stereoselectively. This new C–C bond constructing reaction involves, instead of the expected ethynylation of the CN bond, the addition of azaallyl anions to the triple bond of acetylene.