The Role of Reversible Oxidative Addition in Selective Palladium(0)-Catalyzed Intramolecular Cross-Couplings of Polyhalogenated Substrates: Synthesis of Brominated Indoles
Stephen G. Newman and Mark Lautens*
*Department of Chemistry, University of Toronto, Toronto,
Ontario, Canada M5S 3H6, Email: mlautenschem.utoronto.ca
S. G. Newman, M. Lautens, J. Am. Chem. Soc., 2010, 132, 11416-11417.
DOI: 10.1021/ja1052335
Abstract
A Pd(0)-catalyzed C-N bond-forming reaction enables the synthesis of brominated indoles in the presence of PtBu3 as phosphine ligand. The bulky ligand serves to prevent inhibition of the catalyst by facilitating reversible oxidative addition into the product C-Br bond.
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Key Words
Indoles, Buchwald-Hartwig Coupling
ID: J48-Y2010-2300