Communication

Catalytic C[BOND]H Amination with Unactivated Amines through Copper(II) Amides†

  1. Stefan Wiese1,
  2. Dr. Yosra M. Badiei1,
  3. Raymond T. Gephart1,
  4. Dr. Susanne Mossin3,4,
  5. Dr. Matthew S. Varonka1,
  6. Dr. Marie M. Melzer1,
  7. Prof. Dr. Karsten Meyer3,
  8. Prof. Thomas R. Cundari2,*,
  9. Prof. Timothy H. Warren1,*

Article first published online: 15 SEP 2010

DOI: 10.1002/anie.201003676

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 49, Issue 47, pages 8850–8855, November 15, 2010

Additional Information

How to Cite

Wiese, S., Badiei, Y. M., Gephart, R. T., Mossin, S., Varonka, M. S., Melzer, M. M., Meyer, K., Cundari, T. R. and Warren, T. H. (2010), Catalytic C[BOND]H Amination with Unactivated Amines through Copper(II) Amides. Angew. Chem. Int. Ed., 49: 8850–8855. doi: 10.1002/anie.201003676

Author Information

  1. 1

    Department of Chemistry, Georgetown University, Box 571227, Washington, DC 20057-1227 (USA), Fax: (+1) 202-687-6209

  2. 2

    Department of Chemistry, Center for Advanced Scientific Computing and Modeling (CASCaM), University of North Texas, Denton, TX 78203 (USA)

  3. 3

    Department of Chemistry and Pharmacy, Friedrich-Alexander-University Erlangen-Nürnberg, Egerlandstrasse 1, 91058 Erlangen (Germany)

  4. 4

    Current address: Centre for Catalysis and Sustainable Chemistry, Department of Chemistry, Technical University of Denmark, 2800 Kgs Lyngby (Denmark)

*Department of Chemistry, Center for Advanced Scientific Computing and Modeling (CASCaM), University of North Texas, Denton, TX 78203 (USA)

  1. †

    The authors acknowledge funding from the National Science Foundation (CHE-0716304 to T.H.W.; CHE-0701247 and CHE-0741936 to T.R.C), the Deutsche Forschungsgemeinschaft (SFB 583), the Alexander von Humboldt Foundation (re-invitation award to T.H.W.), and the Chemical Computing Group (MOE software to T.R.C.). Y.M.B. thanks Georgetown University for a Dissertation Fellowship and M.M.M. is grateful to the Luce Foundation for a pre-doctoral fellowship.

Publication History

  1. Issue published online: 11 NOV 2010
  2. Article first published online: 15 SEP 2010
  3. Manuscript Received: 16 JUN 2010

Funded by

  • National Science Foundation. Grant Numbers: CHE-0716304, CHE-0701247, CHE-0741936
  • Deutsche Forschungsgemeinschaft
  • Alexander von Humboldt Foundation
  • Chemical Computing Group

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Keywords:

  • amide;
  • amination;
  • C[BOND]H functionalization;
  • copper
Thumbnail image of graphical abstract

En route to catalysis: Two equivalents of the three-coordinate copper(II) amide [(Cl2NN)Cu]-NHAd participate in stoichiometric C[BOND]H amination by a H-atom abstraction/radical capture sequence. This active species may be generated through a copper(II) tert-butoxide intermediate to allow for the unprecedented catalytic amination of sp3-C[BOND]H bonds with unactivated alkylamines. This method greatly expands the range of amines for catalytic C[BOND]H amination since most protocols require N-based electron-withdrawing groups.

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