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Copper-Catalyzed Hydroamination of Alkynes with Aliphatic Amines: Regioselective Access to (1E,3E)-1,4-Disubstituted-1,3-dienes

Author:
Bahri, Janet, Jamoussi, Bassem, van Der Lee, Arie, Taillefer, Marc, Monnier, Florian
Source:
Organic letters 2015 v.17 no.5 pp. 1224-1227
ISSN:
1523-7052
Subject:
alkynes, amines, chemical bonding, chemical reactions, chemical structure, heterocyclic compounds, regioselectivity
Abstract:
Copper-catalyzed hydroamination of aromatic or heteroaromatic alkynes with cyclic secondary aliphatic amines undergoes generation of an enamine-type intermediate. The latter is transformed in situ via a coupling reaction with a second molecule of alkyne to afford regioselectively (1E,3E)-1,4-disubstituted-1,3-dienes with the formation of C–N, C–C, and C–H bonds.
Agid:
5790282