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:
zlu
rdg.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 (free Supporting Information)
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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
Key Words
Sonogashira Coupling, Cacchi Reaction, Indoles, Multicomponent Reactions
ID: J54-Y2006-2040
