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:
rishi.vaswani
constellationpharma.com
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
Abstract
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.
see article for more examples
Key Words
ID: J54-Y2014
