A Practical Mild, One-Pot, Regiospecific Synthesis of 2,3-Disubstituted Indoles via Consecutive Sonogashira and Cacchi Reactions

Bruce Z. Lu,* Wenyi Zhao, Han-Xun Wei, Marine Dufour, Vittorio Farina and Chris H. Senanayake

*Department of Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc., Suite 205, East Leigh Street, Richmond, Virginia 23219, Email: zlurdg.boehringer-ingelheim.com

B. Z. Lu, W. Zhao, H.-X. Wei, M. Dufour, V. Farina, C. H. Senanayake, Org. Lett., 2006, 8, 3271-3274.

DOI: 10.1021/ol061136q

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Abstract

A practical one-pot, regiospecific three-component process for the synthesis of 2,3-disubstituted indoles based on Cacchi's protocol was developed. This mild Pd-catalyzed domino indolization procedure allows rapid access to various indoles via consecutive Sonogashira coupling, amidopalladation, and reductive elimination.

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reaction pathway

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One-Pot and Regiospecific Synthesis of 2,3-Disubstituted Indoles from 2-Bromoanilides via Consecutive Palladium-Catalyzed Sonogashira Coupling, Amidopalladation, and Reductive Elimination

B. Z. Lu, H.-X. Wei, Y. Zhang, W. Zhao, M. Dufour, G. Li, V. Farina, C. H. Senanayake, J. Org. Chem., 2013, 78, 4558-4562.

Key Words

Sonogashira Coupling, Cacchi Reaction, Indoles, Multicomponent Reactions

ID: J54-Y2006-2040