Synthesis 2016; 48(07): 974-986
DOI: 10.1055/s-0035-1561349
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© Georg Thieme Verlag Stuttgart · New York

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

Jesco Panther
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany   Email: ThomasJJMueller@uni-duesseldorf.de
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Thomas J. J. Müller*
Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany   Email: ThomasJJMueller@uni-duesseldorf.de
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Further Information

Publication History

Received: 12 December 2015

Accepted after revision: 11 January 2016

Publication Date:
04 February 2016 (online)


Dedicated to Prof. Dr. Rolf Gleiter on the occasion of his 80th birthday.

Abstract

Initiated by Heck isomerization of aryl bromides and allyl alcohols, the intermediate 3-arylpropanal is readily transformed into 3-arylmethylindoles by Fischer indole synthesis in a consecutive three-component fashion in moderate to good yields. This Heck isomerization–Fischer indolization (HIFI) sequence can be readily concatenated into a four-component Heck isomerization–Fischer indolization–alkylation (HIFIA) synthesis affording products in good to excellent yields.

Supporting Information

 
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