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Synfacts 2010(1): 0030-0030  
DOI: 10.1055/s-0029-1218464
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Gold-Catalyzed Synthesis of Quinolines

Contributor(s): Victor Snieckus, Cédric Schneider
C. Praveen, S. Jegatheesan, P. T. Perumal*
Central Leather Research Institute, Chennai, India
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

Based on previous results from the Sakai group (InBr3-catalyzed dimerization of 2-ethylanilines: N. Sakai, K. Annaka, T. Konakahara J. Org. Chem. 2006, 71, 3653), the synthesis of quinolines 2 via gold(III)-catalyzed intermolecular dimerization from 2-ethynylaniline 1 is reported. After optimization, the combination of AuCl3 and AgOTf is crucial to obtain the product 2 in good yield. Under these reaction conditions, substrates possessing EWGs or EDGs were tolerated affording the corresponding quinolines in good yields.