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Intramolecular Pd(II)-Catalyzed Oxidative Biaryl Synthesis Under Air: Reaction Development and Scope

Benoît Liégault, Doris Lee, Malcolm P. Huestis, David R. Stuart and Keith Fagnou*

*Center for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, ON, K1N 6J7, Canada, Email: keith.fagnouuottawa.ca

B. Liégault, D. Lee, M. P. Huestis, D. R. Stuart, K. Fagnou, J. Org. Chem., 2008, 73, 5022-5028.

DOI: 10.1021/jo800596m (free Supporting Information)



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Abstract

An intramolecular palladium(II)-catalyzed oxidative carbon-carbon bond formation under air in the presence of pivalic acid as the reaction solvent, instead of acetic acid, results in greater reproducibility, higher yields, and broader substrate scope. The reaction allows the conversion of both electron-rich and electron-deficient diarylamines.

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Key Words

Carbazoles, Dibenzofurans, Oxygen


ID: J42-Y2008-1780