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Synthesis 2010(23): 4033-4042  
DOI: 10.1055/s-0030-1258284
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Nonsymmetrical 5-Aryl-2-indolopyrrole Derivatives via Controlled Mono Suzuki-Miyaura Cross-Coupling on N-Boc-2,5-dibromopyrrole

Floriane Beaumard, Philippe Dauban, Robert H. Dodd*
Institut de Chimie des Substances Naturelles, UPR 2301, Campus de Recherche de Gif, Centre National de la Recherche Scientifique, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France
Fax: +33(1)69077247; e-Mail: robert.dodd@icsn.cnrs-gif.fr;
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Publication History

Received 3 August 2010
Publication Date:
05 October 2010 (online)

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Abstract

The first example of mono Suzuki-Miyaura cross-coupling of N-Boc-2,5-dibromopyrrole with a boronic acid (indol-2-ylboronic acid) is reported. The resulting 2-indolyl-5-bromopyrrole derivative was in turn coupled with a variety of aryl- or heteroarylboronic acids thereby providing the corresponding non-symmetrical 2,5-disubstituted pyrroles in good to excellent yields. The tert-butoxycarbonyl (Boc) groups could be easily removed to give the completely deprotected products.

Key words

cross-coupling - Suzuki-Miyaura - indole - pyrrole - palladium-catalyzed