New Three-Component Glyoxylation-Decarbonylative
Stille Coupling Sequence to Acyl Heterocycles under Mild
Conditions

Boris O. A. Tasch; Eugen Merkul; Walter Frank; Thomas J. J. Müller

doi:10.1055/s-0029-1218802

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Synthesis 2010(13): 2139-2146
DOI: 10.1055/s-0029-1218802

PAPER

New Three-Component Glyoxylation-Decarbonylative Stille Coupling Sequence to Acyl Heterocycles under Mild Conditions

Boris O. A. Tasch^a, Eugen Merkul^a, Walter Frank^b, Thomas J. J. Müller*^a
^a Heinrich-Heine-Universität Düsseldorf, Institut für Organische Chemie und Makromolekulare Chemie, Universitätsstr. 1, 40225 Düsseldorf, Germany
^b Heinrich-Heine-Universität Düsseldorf, Institut für Anorganische Chemie und Strukturchemie, Universitätsstr. 1, 40225 Düsseldorf, Germany
Fax: +49(211)8114324; e-Mail: ThomasJJ.Mueller@uni-duesseldorf.de;

Further Information

Publication History

Received 15 April 2010
Publication Date:
27 May 2010 (online)

Abstract
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Abstract

A consecutive sequence of glyoxylation of 1-methyl-1H-indole, 1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridine or N-substituted pyrroles with oxalyl chloride and subsequent decarbonylative Stille coupling under very mild, Lewis acid free conditions using all reactants in equimolar quantities is reported. As an illustration, this glyoxylation-decarbonylative coupling sequence was elaborated into a consecutive, four-component synthesis of 1-methyl-3-(1-methyl-4,5-dihydro-1H-pyrazol-3-yl)-1H-indole.

Key words

glyoxylation - decarbonylative Stille reaction - multicomponent reaction - C-C coupling - acyl heterocycles

References

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CCDC 775726 (compound 3b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].