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, Bruker-Nonius B.V., Oostsingel 209, 2612 HL Delft, The Netherlands, and Cytec Canada Inc., P.O. Box 240, Niagara Falls, Ontario, Canada L2E 6T4
J. Org. Chem., 2004, 69 (22), pp 7635–7639
DOI: 10.1021/jo048875+
Publication Date (Web): September 30, 2004
Copyright © 2004 American Chemical Society

Abstract

Abstract Image

A 15-member library of phosphaadamantane ligands has been prepared via P-arylation of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phosphaadamantane. Screening of this tertiary phosphine collection has allowed for the rapid determination of the most suitable ligand, specifically 1,3,5,7-tetramethyl-6-(2,4-dimethoxyphenyl)-2,4,8-trioxa-6-phosphaadamantane, for facilitating Suzuki-type couplings of alkyl halides or tosylates containing β-hydrogens with either boronic acids or alkylboranes.

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History

  • Published In Issue October 29, 2004
  • Received July 2, 2004

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