Solid Acid-Catalysed Michael-Type Conjugate Addition of Indoles to Electron-Poor CC Bonds: Towards High Atom Economical Semicontinuous Processes

In this paper a novel application of solid acid catalysts in the chemoselective Friedel–Crafts (FC) alkylation of indoles is reported. The optimal protocol allows highly functionalised indolyl compounds to be synthesised in excellent yields through conjugate addition of indoles with α,β‐unsaturated...

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Veröffentlicht in:Advanced synthesis & catalysis 2004-04, Vol.346 (5), p.545-548
Hauptverfasser: Bandini, Marco, Fagioli, Matteo, Umani-Ronchi, Achille
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Sprache:eng
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Zusammenfassung:In this paper a novel application of solid acid catalysts in the chemoselective Friedel–Crafts (FC) alkylation of indoles is reported. The optimal protocol allows highly functionalised indolyl compounds to be synthesised in excellent yields through conjugate addition of indoles with α,β‐unsaturated ketones and nitro compounds. Finally, the use of commercial Amberlyst‐15 as the heterogeneous catalyst for highly atom efficient continuous and semicontinuous Friedel–Crafts processes is described.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200303213