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Three- and Four-Component Syntheses of 3-Arylmethylindoles by Microwave-Assisted One-Pot Heck Isomerization-Fischer Indolization (Alkylation) (HIFI and HIFIA) Sequences

Jesco Panther, Thomas J. J. Müller*

*Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany, Email: ThomasJJMuelleruni-duesseldorf.de

J. Panther, T. J. J. Müller, Synthesis, 2016, 48, 974-986.

DOI: 10.1055/s-0035-1561349 (free Supporting Information)


 
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Abstract

Heck isomerization of aryl bromides and allyl alcohols provides 3-arylpropanals, that can readily be transformed into 3-arylmethylindoles by Fischer indole synthesis in a consecutive three-component fashion in good yields. This sequence can be expanded to a four-component Heck isomerization-Fischer indolization-alkylation (HIFIA) synthesis.

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Key Words

alkylations, Heck reaction, Fischer indole synthesis, microwave synthesis, indoles


ID: J66-Y2016