Communication

Synthesis of 3-Fluoro-3-aryl Oxindoles: Direct Enantioselective α Arylation of Amides†

  1. Linglin Wu1,
  2. Laura Falivene2,
  3. Dr. Emma Drinkel1,
  4. Sharday Grant1,
  5. Priv.-Doz. Dr. Anthony Linden1,
  6. Prof. Dr. Luigi Cavallo2,4,
  7. Prof. Dr. Reto Dorta1,3,*

Article first published online: 6 FEB 2012

DOI: 10.1002/anie.201200206

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 12, pages 2870–2873, March 19, 2012

Additional Information

How to Cite

Wu, L., Falivene, L., Drinkel, E., Grant, S., Linden, A., Cavallo, L. and Dorta, R. (2012), Synthesis of 3-Fluoro-3-aryl Oxindoles: Direct Enantioselective α Arylation of Amides . Angew. Chem. Int. Ed., 51: 2870–2873. doi: 10.1002/anie.201200206

Author Information

  1. 1

    Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)

  2. 2

    Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084 Fisciano (Italy)

  3. 3

    New address: School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, Crawley 6009 (Australia)

  4. 4

    New address: King Abdullah University of Science and Technology (KAUST), Chemical and Life Sciences and Engineering, KAUST Catalysis Center, Thuwal 23955-6900 (Saudi Arabia)

*Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich (Switzerland)

  1. †

    Support from the Swiss National Science Foundation (LW) is gratefully acknowledged.

Publication History

  1. Issue published online: 13 MAR 2012
  2. Article first published online: 6 FEB 2012
  3. Manuscript Received: 10 JAN 2012

Funded by

  • Swiss National Science Foundation

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Keywords:

  • asymmetric catalysis;
  • N-heterocyclic carbenes;
  • oxindoles;
  • palladium;
  • synthetic methods
Thumbnail image of graphical abstract

Modus operandi: Catalytic access to the title compounds through a new asymmetric α-arylation protocol is reported (see scheme). These products are formed in good yields and excellent enantioselectivities by using a new and easily synthesized chiral N-heterocyclic carbene (NHC) ligand. Advanced DFT calculations reveal the properties of the NHC ligand and the mode of operation of the catalyst.

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