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

Yu Chen, Xiaoan Xie and Dawei Ma*

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: madwmail.sioc.ac.cn

Y. Chen, X. Xie, D. Ma, J. Org. Chem., 2007, 72, 9329-9334.

DOI: 10.1021/jo702059q (free Supporting Information)


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Abstract

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

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Assembly of Conjugated Enynes and Substituted Indoles via CuI/Amino Acid-Catalyzed Coupling of 1-Alkynes with Vinyl Iodides and 2-Bromotrifluoroacetanilides

F. Liu, D. Ma, J. Org. Chem., 2007, 72, 4844-4850.


Key Words

Indoles


ID: J42-Y2007-3680