Communication

Transition-Metal-Free Synthesis of Aryl-Substituted tert-Butyl Ynol Ethers through Addition/Elimination Substitution at an sp Centre

  1. Vincent J. Gray,
  2. Dr. Ben Slater,
  3. Dr. Jonathan D. Wilden*

Article first published online: 19 OCT 2012

DOI: 10.1002/chem.201203015

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 18, Issue 49, pages 15582–15585, December 3, 2012

Additional Information

How to Cite

Gray, V. J., Slater, B. and Wilden, J. D. (2012), Transition-Metal-Free Synthesis of Aryl-Substituted tert-Butyl Ynol Ethers through Addition/Elimination Substitution at an sp Centre. Chem. Eur. J., 18: 15582–15585. doi: 10.1002/chem.201203015

Author Information

  1. Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ (UK)

*Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ (UK)

Publication History

  1. Issue published online: 23 NOV 2012
  2. Article first published online: 19 OCT 2012
  3. Manuscript Received: 24 AUG 2012

Funded by

  • UCL

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Keywords:

  • alkynes;
  • elimination;
  • sp substitution;
  • sulfonamides;
  • synthetic methods
Thumbnail image of graphical abstract

Nucleophilic attack of an alkoxide on an alkynyl sulfonamide leads to displacement of the sulfonamide at the sp centre and isolation of the ynol ether in good yield in a single operation (see scheme). The mechanistic pathway has been probed by the use of coordinating additives, 13C-labelling experiments and ab initio calculations, which indicated that an addition/elimination mechanism is in operation.

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