Communication

Catalytic Generation of Arynes and Trapping by Nucleophilic Addition and Iodination

  1. Prof. Dr. Toshiyuki Hamura1,*,
  2. Yu Chuda1,
  3. Yuya Nakatsuji1,
  4. Prof. Dr. Keisuke Suzuki2,*

Article first published online: 22 FEB 2012

DOI: 10.1002/anie.201108415

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 14, pages 3368–3372, April 2, 2012

Additional Information

How to Cite

Hamura, T., Chuda, Y., Nakatsuji, Y. and Suzuki, K. (2012), Catalytic Generation of Arynes and Trapping by Nucleophilic Addition and Iodination. Angew. Chem. Int. Ed., 51: 3368–3372. doi: 10.1002/anie.201108415

Author Information

  1. 1

    Department of Chemistry, School of Science and Technology, Kwansei Gakuin University and PRESTO, JST Agency, 2-1 Gakuen, Sanda, Hyogo 669-1337 (Japan)

  2. 2

    Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan)

*Department of Chemistry, School of Science and Technology, Kwansei Gakuin University and PRESTO, JST Agency, 2-1 Gakuen, Sanda, Hyogo 669-1337 (Japan)

Publication History

  1. Issue published online: 27 MAR 2012
  2. Article first published online: 22 FEB 2012
  3. Manuscript Revised: 24 DEC 2011
  4. Manuscript Received: 29 NOV 2011

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Keywords:

  • arenes;
  • arynes;
  • iodine;
  • lithiation;
  • regioselectivity
Thumbnail image of graphical abstract

A fair exchange: In the title reaction, alkynyllithium serves as an initiator for benzyne generation through an iodine–lithium exchange (see scheme; Tf=trifluoromethanesulfonyl). When performed in the presence of stoichiometric amounts of a nucleophile, the generated benzyne undergoes attack by lithio nucleophiles to generate aryllithium, which is then iodinated by iodoalkyne to give the iodoarenes 1.

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