High-yield syntheses of sterically demanding bis(N-heterocyclic carbene) complexes of palladium

Organometallics

Volumn 18, Issue 20, 1999, Pages 4082-4089

  Herrmann, Wolfgang A ^a   Schwarz, Jürgen ^a   Gardiner, Michael G ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000371187     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990326k     Document Type: Article

References (36)

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4. Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem. 1995, 107, 2602; Angew. Chem., Int. Ed. Engl. 1995, 34, 2371. For a theoretical study on this system, see: Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608.
5. Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem. 1995, 107, 2602; Angew. Chem., Int. Ed. Engl. 1995, 34, 2371. For a theoretical study on this system, see: Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608.
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10. For initial papers in the field, see: (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414. (b) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049. (c) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849. For theoretical interpretations relating to this matter, see: (d) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177. (e) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581.
11. For initial papers in the field, see: (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414. (b) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049. (c) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849. For theoretical interpretations relating to this matter, see: (d) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177. (e) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581.
12. For initial papers in the field, see: (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414. (b) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049. (c) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849. For theoretical interpretations relating to this matter, see: (d) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177. (e) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581.
13. For initial papers in the field, see: (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414. (b) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049. (c) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849. For theoretical interpretations relating to this matter, see: (d) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177. (e) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581.
14. For initial papers in the field, see: (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414. (b) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049. (c) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849. For theoretical interpretations relating to this matter, see: (d) Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177. (e) Froese, R. D. J.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 1581.
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19. A decomposition pathway for cationic (imidazolin-2-ylidene)-palladium methyl complexes has recently been recognized, whereby a 2-alkylimidazolium salt and reduced palladium(0) species are formed: McGuinness, D. S.; Green, M. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1998, 565, 165. We report no evidence for the formation of such species here during our synthetic procedure.
20. 13C NMR spectra for complexes 3, and impurities of complexes 4 prevented accurate microanalyses of complexes 3.
21. 2-: Ortwerth, M. F.; Wyzlic, M. J.; Baughman, R. G. Acta Crystallogr. 1998, C54, 1594.
22. 2-: Ortwerth, M. F.; Wyzlic, M. J.; Baughman, R. G. Acta Crystallogr. 1998, C54, 1594.
23. 2-: Ortwerth, M. F.; Wyzlic, M. J.; Baughman, R. G. Acta Crystallogr. 1998, C54, 1594.
24. Although the 10-membered ring formed due to H-bonding is believed to be stable in solution, fluxionality in the ring is apparently due to the singlet resonance observed for the methylene hydrogens in the complex at room temperature.
25. 2), 7.50-7.90 (14 H, br, CH(imid), CH(Ph)).
26. Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Hermann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Submitted for publication.
27. Gardiner, M. G.; Herrmann, W. A.; Schwarz, J. Unpublished results.
28. 2 (596.62): C, 38.25, H, 3.04; N, 14.09.
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