Pd-Catalyzed Tandem C-N/C-C Coupling of gem-Dihalovinyl Systems: A Modular Synthesis of 2-Substituted Indoles
Yuan-Qing Fang and Mark Lautens*
*Davenport Chemistry Laboratories, Department of Chemistry, University of
Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada, Email:
mlautens
chem.utoronto.ca
Y.-Q. Fang, M. Lautens, Org. Lett., 2005, 7, 3549-3552.
DOI: 10.1021/ol051286l
Abstract
The Pd-catalyzed tandem C-N/Suzuki-Miyaura coupling of readily prepared ortho-gem-dihalovinylanilines with boronic acids, esters, alkyl 9-BBN derivatives, and trialkylboranes gave 2-substituted indoles in good to excellent yields. Optimal conditions used low loadings of a Pd(OAc)2/S-Phos catalyst in the presence of K3PO4·H2O.
see article for more examples
see article for more reactions
Synthesis of 2-Vinylic Indoles and Derivatives via a Pd-Catalyzed Tandem Coupling Reaction
A. Fayol, Y.-Q. Fang, M. Lautens, Org. Lett., 2006, 8, 4203-4206.
Key Words
Suzuki Coupling, Buchwald-Hartwig Amination, Indoles
ID: J54-Y2005-1050
