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A Practical Synthesis of Indoles via a Pd-Catalyzed C-N Ring Formation

Rishi G. Vaswani*, Brian K. Albrecht, James E. Audia, Alexandre Côté, Les A. Dakin, Martin Duplessis, Victor S. Gehling, Jean-Christophe Harmange, Michael C. Hewitt, Yves Leblanc, Christopher G. Nasveschuk and Alexander M. Taylor

*Department of Chemistry, Constellation Pharmaceuticals, Inc., 215 First Street, Suite 200, Cambridge, Massachusetts 02142, United States, Email:

R. G. Vaswani, B. K. Albrecht, J. E. Audia, A. Côté, L. A. Dakin, M. Duplessis, V. S. Gehling, J.-C. Harmange, M. C. Hewitt, Y. Leblanc, C. G. Nasveschuk, A. M. Taylor, Org. Lett., 2014, 16, 4114-4117.

DOI: 10.1021/ol5018118


A Pd-catalyzed C-N bond coupling of various halo-aryl enamines enables the synthesis of N-functionalized C2-/C3-substituted indoles. Optimized conditions comprising the RuPhos precatalyst and RuPhos in the presence of NaOMe in 1,4-dioxane tolerate a variety of substituents and are scalable for the construction of indoles in multigram quantities.

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ID: J54-Y2014