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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 (free Supporting Information)


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