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TIMENtol/3,5xyl: Unexpected Reactivity Resulting From Modifications of the Ligand Periphery

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High- and Low-Valent tris-N-Heterocyclic Carbene Iron Complexes

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Abstract

Coordinatively unsaturated, electron-rich metal centers have proven to be powerful species for small molecule activation and functionalization. Due to their ?-donor and ?-accepting properties, N-heterocyclic carbene (NHC) ligands are particularly suitable for the synthesis of a variety of low- to high-valent metal complexes; thus, they are perfectly suitable to act as supporting ligands for small molecule activation in reactive coordination complexes. The steric bulk of NHC ligands is highly tunable and a variety of ligands can be conveniently synthesized.

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References

  1. W.B. Tolman (ed.), Activation of Small Molecules: Organometallic and Bioinorganic Perspectives (Wiley-VCH, Weinheim, 2006)

    Google Scholar 

  2. M. Alcarazo, T. Stork, A. Anoop, W. Thiel, A. Fürstner, Angew. Chem. Int. Ed. 49, 2542 (2010)

    Article  CAS  Google Scholar 

  3. X. Hu, I. Castro-Rodriguez, K. Olsen, K. Meyer, Organometallics 23, 755 (2004)

    Google Scholar 

  4. F.E. Hahn, M.C. Jahnke, Angew. Chem. Int. Ed. 47, 3122 (2008)

    Article  CAS  Google Scholar 

  5. X. Hu, K. Meyer, J. Organomet. Chem. 690, 5474 (2005)

    Google Scholar 

  6. O. Einsle, F.A. Tezcan, S.L.A. Andrade, B. Schmid, M. Yoshida, J.B. Howard, D.C. Rees, Science 297, 1696 (2002)

    Google Scholar 

  7. M. Aliaga-Alcalde, S.D. George, B. Mienert, E. Bill, K. Wieghardt, F. Neese, Angew. Chem. Int. Ed. 44, 2908 (2005)

    Article  CAS  Google Scholar 

  8. C. Vogel, F.W. Heinemann, J. Sutter, C. Anthon, K. Meyer, Angew. Chem. Int. Ed. 47, 2681 (2008)

    Article  CAS  Google Scholar 

  9. J.J. Scepaniak, M.D. Fulton, R.P. Bontchev, E.N. Duesler, M.L. Kirk, J.M. Smith, J. Am. Chem. Soc. 130, 10515 (2008)

    Google Scholar 

  10. J.J. Scepaniak, J. Young, R. Bontchev, J.M. Smith, Angew. Chem. Int. Ed. 48, 3158 (2009)

    Article  CAS  Google Scholar 

  11. C.S. Vogel, F.W. Heinemann, M.M. Khusniyarov, K. Meyer, Inorg. Chim. Acta. 364, 226 (2010)

    Google Scholar 

  12. X. Hu, K. Meyer, J. Am. Chem. Soc. 126, 16322 (2004)

    Google Scholar 

  13. A.J. Arduengo III, F.P. Gentry Jr, P.K. Taverkere, H.E. Simmons III. (E. I. Du Pont de Nemours & Co., USA) US 6177575, 7 (2001)

    Google Scholar 

  14. K. Ward Jr, J. Am. Chem. Soc. 57, 914 (1935)

    Google Scholar 

  15. X. Hu, I. Castro-Rodriguez, K. Meyer, J. Am. Chem. Soc. 126, 13464 (2004)

    Google Scholar 

  16. M. Brookhart, M.L.H. Green, G. Parkin, Proc. Natl. Acad. Sci. 104, 6908 (2007)

    Google Scholar 

  17. P.B. Hitchcock, M.F. Lappert, P. Terreros, J. Organomet. Chem. 239, C26 (1982)

    Google Scholar 

  18. F. Neese, ORCA—an Ab Initio, Density Functional and Semiempirical SCF-MO Package, version 2.7 revision 0; Institut für Physikalische und Theoretische Chemie (Universität Bonn, Germany, 2009)

    Google Scholar 

  19. A.D. Becke, Phys. Rev. A 38, 3098 (1988)

    Google Scholar 

  20. J.P. Perdew, Phys. Rev. B 33, 8822 (1986)

    Google Scholar 

  21. J.P. Perdew, Phys. Rev. B 34, 7406 (1986)

    Google Scholar 

  22. A.D. Becke, J. Chem. Phys. 98, 5648 (1993)

    Google Scholar 

  23. C.T. Lee, W.T. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988)

    Google Scholar 

  24. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, J. Phys. Chem. 98, 11623 (1994)

    Google Scholar 

  25. D. Bourissou, O. Guerret, F.P. Gabbaie, G. Bertrand, Chem. Rev. 100, 39 (2000)

    Google Scholar 

  26. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 97, 2571 (1992)

    Google Scholar 

  27. F. Neese, Inorg. Chim. Acta 337, 181 (2002)

    Google Scholar 

  28. S. Sinnecker, L.D. Slep, E. Bill, F. Neese, Inorg. Chem. 44, 2245 (2005)

    Article  CAS  Google Scholar 

  29. S. Portmann, Molekel, version 4.3.win32, CSCS/UNI Geneva, Switzerland (2002)

    Google Scholar 

  30. SADABS 2.06, Bruker AXS, Inc., Madison WI., U.S.A (2002)

    Google Scholar 

  31. SHELXTL NT 6.12, Bruker AXS, Inc., Madison WI., U.S.A (2002)

    Google Scholar 

  32. C.S. Vogel, F.W. Heinemann, M.M. Khusniyarov, K. Meyer, Unexpected reactivity resulting from modifications of the ligand periphery: Synthesis, structure, and spectroscopic properties of iron complexes of new tripodal N-heterocyclic carbene (NHC) ligands, Inorganica Chimica Acta 364, 226–237 (2010) (invited article to special issue in honor of Prof. Dr. A.L. Rheingold)

    Google Scholar 

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Acknowledgments

Text, schemes, and figures of this chapter, in part, are reprints of the materials published in the following paper Vogel et al. [32]. The dissertation author was the primary researcher and author. The co-authors listed in the publication also participated in the research. The permission to reproduce the paper was granted by Elsevier. Copyright 2010, Elsevier.

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Correspondence to Carola S. Vogel .

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Vogel, C.S. (2012). TIMENtol/3,5xyl: Unexpected Reactivity Resulting From Modifications of the Ligand Periphery. In: High- and Low-Valent tris-N-Heterocyclic Carbene Iron Complexes. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-27254-7_3

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