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Phosphaadamantanes as Ligands for Palladium Catalyzed Cross-Coupling Chemistry: Library Synthesis, Characterization, and Screening in the Suzuki Coupling of Alkyl Halides and Tosylates Containing β-Hydrogens with Boronic Acids and Alkylboranes

Tim Brenstrum, David A. Gerristma, George M. Adjabeng, Christopher S. Frampton, James Britten, Alan J. Robertson, James McNulty and Alfredo Capretta*

*Department of Chemistry, McMaster University, Hamilton, Ontario, Canada L8S 4M1, Email: caprettamcmaster.ca

T. Brenstrum, D. A. Gerristma, G. M. Adjabeng, C. S. Frampton, J. Britten, A. J. Robertson, J. McNulty, A. Capretta, J. Org. Chem., 2004, 69, 7635-7639.

DOI: 10.1021/jo048875+ (free Supporting Information)



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Abstract

Screening of a 15-member library of phosphaadamantane ligands has allowed for the rapid determination of the most suitable ligand for facilitating Suzuki-type couplings of alkyl halides or tosylates containing β-hydrogens with either boronic acids or alkylboranes.

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Key Words

Suzuki Coupling, Arenes, Alkanes


ID: J42-Y2004-1170