Facile Access to Polysubstituted Indoles via a Cascade Cu-Catalyzed Arylation−Condensation Process

Yu Chen, Xiaoan Xie, and Dawei Ma*
Department of Chemistry, Fudan University, Shanghai 200433, China, and State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China
J. Org. Chem., 2007, 72 (24), pp 9329–9334
DOI: 10.1021/jo702059q
Publication Date (Web): November 2, 2007
Copyright © 2007 American Chemical Society

Abstract

Abstract Image

CuI/l-proline-catalyzed cross-coupling of 2-halotrifluoroacetanilides with β-keto esters and amides followed by in situ acidic hydrolysis delivered 2,3-disubstituted indoles. The halides bearing a strong electron-withdrawing group in the 4-position can undergo in situ basic hydrolysis to provide the corresponding indoles. Polysubstituted indoles can be prepared from substituted 2-halotrifluoroacetanilides with high regioselectivity.

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History

  • Published In Issue November 23, 2007
  • Received September 19, 2007

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