Communication

Higher-Order Zincates as Transmetalators in Alkyl–Alkyl Negishi Cross-Coupling†

  1. Lucas C. McCann1,
  2. Dr. Howard N. Hunter1,
  3. Prof. Dr. Jason A. C. Clyburne2,
  4. Prof. Dr. Michael G. Organ1,*

Article first published online: 8 JUN 2012

DOI: 10.1002/anie.201203547

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 28, pages 7024–7027, July 9, 2012

Additional Information

How to Cite

McCann, L. C., Hunter, H. N., Clyburne, J. A. C. and Organ, M. G. (2012), Higher-Order Zincates as Transmetalators in Alkyl–Alkyl Negishi Cross-Coupling . Angew. Chem. Int. Ed., 51: 7024–7027. doi: 10.1002/anie.201203547

Author Information

  1. 1

    Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada) http://www.yorku.ca/organ/

  2. 2

    Department of Chemistry, Saint Mary's University, Halifax, Nova Scotia, B3H 3C3 (Canada)

*Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3 (Canada) http://www.yorku.ca/organ/

  1. †

    This work was supported by NSERC (Canada) and The Ontario Research Fund (ORF) (Ontario).

Publication History

  1. Issue published online: 4 JUL 2012
  2. Article first published online: 8 JUN 2012
  3. Manuscript Received: 8 MAY 2012

Funded by

  • NSERC (Canada)
  • The Ontario Research Fund (ORF) (Ontario)

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Keywords:

  • cross-coupling;
  • Negishi reaction;
  • palladium;
  • transmetalation;
  • zincates
Thumbnail image of graphical abstract

Negishi revisited: Higher-order alkyl zincates have been subjected to Negishi coupling with alkyl bromides. For the first time, coupling takes place in straight THF, i.e., without a salt additive and a high dielectric co-solvent. This provides evidence that it is the higher-order zincate that undergoes transmetalation to Pd, and not mono-anionic zincates or any of the other species present in the Schlenk equilibrium.

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