A palladium- and copper-free cross-coupling of ethyl 3-halo-2-propynoates with 4,5,6,7-tetrahydroindoles on alumina

Ethyl 3-halo-2-propynoates undergo facile (no heating, no base, no solvent) palladium- and copper-free cross-coupling with 4,5,6,7-tetrahydroindoles on alumina to afford the corresponding 4,5,6,7-tetrahydroindole-2-propynoates in 46% and 71% yields. The yield of the by-products [ethyl 3,3-di(4,5,6,7...

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Bibliographic Details
Published in:Tetrahedron letters 2007-07, Vol.48 (27), p.4661-4664
Main Authors: Trofimov, B.A., Sobenina, L.N., Demenev, A.P., Stepanova, Z.V., Petrova, O.V., Ushakov, I.A., Mikhaleva, A.I.
Format: Article
Language:English
Subjects:
4,5,6,7-Tetrahydroindole-2-propynoates
4,5,6,7-Tetrahydroindoles
Alumina
Cross-coupling
Ethyl 3,3-di(4,5,6,7-tetrahydro-1 H-indol-2-yl)acrylates
Ethyl 3-halo-2-propynoates
Pyrroles
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Summary:Ethyl 3-halo-2-propynoates undergo facile (no heating, no base, no solvent) palladium- and copper-free cross-coupling with 4,5,6,7-tetrahydroindoles on alumina to afford the corresponding 4,5,6,7-tetrahydroindole-2-propynoates in 46% and 71% yields. The yield of the by-products [ethyl 3,3-di(4,5,6,7-tetrahydro-1 H-indol-2-yl)acrylates] under appropriate conditions can reach 79%.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.05.027