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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

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1365-3075
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Volume 83, Issue 3 (Feb 2011)

Issues

An oxidative carbon–carbon bond-forming reaction proceeds via an isolable iminium ion

Althea S.-K. Tsang
  • Corresponding author
  • School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia
  • Other articles by this author:
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/ Paul Jensen
  • Corresponding author
  • School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia
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/ James M. Hook
  • Corresponding author
  • NMR Facility, Analytical Centre, University of New South Wales, Sydney, NSW 2052, Australia
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/ A. Stephen K. Hashmi
  • Corresponding author
  • Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
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/ Matthew H. Todd
  • Corresponding author
  • School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia
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Published Online: 2011-02-07 | DOI: https://doi.org/10.1351/PAC-CON-11-01-01

The mechanism of our previously reported DDQ-mediated oxidative C–C bond-forming reaction is investigated. We are able to trap and characterize an iminium ion intermediate with X-ray crystallography, elemental analysis, and solid-state NMR spectroscopy; to our knowledge this is the first time this putative intermediate ion has been directly observed in such cross-dehydrogenative couplings (CDCs). The intermediate can be reacted with a range of nucleo-philes, including a malonate that is not amenable to a one-pot reaction protocol.

Keywords: DDQ; iminium ion; mechanism; oxidative coupling; C–C bond formation

Conference

International Conference on Organic Synthesis (ICOS-18), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 18th, Bergen, Norway, 2010-08-01–2010-08-06

References

About the article

Published Online: 2011-02-07

Published in Print: 2011-02-07


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-11-01-01.

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