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

Several imines, readily derived from aryl methyl ketones and benzylamines, react with acetylene gas in KOBu /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...

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Bibliographic Details
Published in:Organic letters 2020-04, Vol.22 (7), p.2611-2614
Main Authors: Bidusenko, Ivan A, Schmidt, Elena Yu, Protsuk, Nadezhda I, Ushakov, Igor A, Vashchenko, Alexander V, Afonin, Andrei V, Trofimov, Boris A
Format: Article
Language:English
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Summary:Several imines, readily derived from aryl methyl ketones and benzylamines, react with acetylene gas in KOBu /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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00564