Preparation of Annulated Nitrogen-Containing Heterocycles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Sequence

A palladium-catalyzed/norbornene-mediated sequential coupling reaction involving an aromatic sp2 C−H functionalization as the key step is described, in which an alkyl−aryl bond and an aryl−heteroaryl bond are formed in one pot. A variety of highly substituted six- and seven-membered annulated pyrrol...

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Bibliographic Details
Published in:Organic letters 2006-05, Vol.8 (10), p.2043-2045
Main Authors: Blaszykowski, Christophe, Aktoudianakis, Evangelos, Bressy, Cyril, Alberico, Dino, Lautens, Mark
Format: Article
Language:English
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Summary:A palladium-catalyzed/norbornene-mediated sequential coupling reaction involving an aromatic sp2 C−H functionalization as the key step is described, in which an alkyl−aryl bond and an aryl−heteroaryl bond are formed in one pot. A variety of highly substituted six- and seven-membered annulated pyrroles and pyrazoles were synthesized in a one-step process in good yields from readily accessible N-bromoalkyl pyrroles or pyrazoles and aryl iodides.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060447y