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

Ivan A BidusenkoElena Yu SchmidtNadezhda I ProtsukIgor A UshakovAlexander V VashchenkoAndrei V Afonin Boris A Trofimov

Published in: Organic letters (2020)

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.

Keyphrases

room temperature
transition metal
ionic liquid
electron transfer
carbon dioxide