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

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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

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ID: J48-Y2010-2300