Diphosphinine derivatives of terpyridine: A new class of neutral π-accepting PNP-pincer ligands

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 8803-8807

  Müller, Christian ^a   Pidko, Evgeny A ^a   Lutz, Martin ^b   Spek, Anthony L ^b   Vogt, Dieter ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Coordination chemistry; Copper; Density functional calculations; Heterocycles; Phosphorus

Indexed keywords

COORDINATION REACTIONS; COPPER; METAL COMPLEXES; METALLIC COMPOUNDS; OPTOELECTRONIC DEVICES; PHOSPHORUS; REACTION KINETICS; TRANSITION METALS;

COORDINATION CHEMISTRY; COORDINATION MODES; DENSITY FUNCTIONAL CALCULATIONS; DONOR ATOMS; HETEROCYCLES; HOMOGENEOUS CATALYSIS; METAL CENTERS; NEW CLASSES; NOVEL LIGANDS; PHOSPHININE; PINCER LIGANDS; PINCER SYSTEMS; PYRIDINE MOIETIES; TERPYRIDINE; TETRAHEDRAL COORDINATION GEOMETRIES; TRIDENTATE LIGANDS;

LIGANDS;

COPPER; LIGAND; PHOSPHINE; PHOSPHINE DERIVATIVE; PURINE NUCLEOSIDE PHOSPHORYLASE; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; DIMERIZATION; ENZYME SPECIFICITY; METABOLISM;

COPPER; DIMERIZATION; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHINES; PURINE-NUCLEOSIDE PHOSPHORYLASE; PYRIDINES; SUBSTRATE SPECIFICITY;

EID: 55049094525     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801337     Document Type: Article

References (45)

1. a) G. Märkl, Angew. Chem. 1966, 78, 907;
2. b) A. J. Ashe III. J. Am. Chem. Soc. 1971, 93, 3293.
3. For recent reviews see: a) C. Müller. D. Vogt, Dalton Trans. 2007, 5505-5523:
4. b) P. Le Floch, Coord. Chem. Rev. 2006, 250, 627-681:
5. c) F. Mathey, P. Le Floch, Sci. Synth. 2005, 15, 1097-1155;
6. d) F. Mathey, Angew. Chem. 2003, 115, 1616-1643;
7. Angew. Chem. Int. Ed. 2003, 42, 1578-1604;
8. e) P. Le Floch, F. Mathey. Coord. Chem. Rev. 1998, 179-180, 771-791.
9. a) C. Müller, E. A. Pidko, A. J. P. M. Staring, M. Lulz, A. L. Spek, R. A. van Santen, D. Vogt, Chem. Eur. J. 2008, 14, 4899-4905;
10. b) C. Müller, Z. Freixa, M. Lutz, A. L. Spek, D. Vogt, P. W. N. M. van Leeuwen, Organometallics 2008, 27, 834-838;
11. c) C. Müller, E. A. Pidko, D. Totev, M. Lutz, A. L. Spek, R. A. van Santen. D. Vogt, Dalton Trans. 2007, 5372-5375;
12. d) C. Müller, D. Wasserberg, J. J. M. Weemers, E. A. Pidko, S. Hoffmann, M. Lutz, A. L. Spek, S. C. J. Meskers, R. A. Janssen, R. A. van Santen, D. Vogt. Chem. Eur. J. 2007, 13, 4548-4559;
13. e) C. Müller, M. Lutz, A. L. Spek, D. J. Vogt, J. Chem. Crystallogr. 2006, 36, 869-874:
14. f) C. Müller, L. Guarrotxena-Lopéz, H. Kooijman, A. L. Spek, D. Vogl, Tetrahedron Lett. 2006, 47, 2017-2020.
15. B. Breit. R. Winde, T. Mackewitz, R. Paciello, K. Harms, Chem. Eur.J. 2001, 7, 3106-3121.
16. For the synthesis of substituted terpyridines starting from diacetylpyridine see: E. C. Constable, E. Figgemeier. I.A. Hougen, C. E. Housecroft, M. Neuburger, S. Schaffner, L. A. Whall. Dalton Trans. 2005, 1168-1175.
17. J. W. Ellis, K. N. Harrison, P. A. T. Hoye, A. G. Orpen, P. G. Pringle, M. B. Smith, Inorg. Chem. 1992, 31, 3026-3033.
18. E. Niecke, H. Westermann, Synthesis 1988, 330.
19. 2-based PNP ligands see for example: a) C. Hahn, M. Cucciolito, A. Vitagliano, J. Am. Chem. Soc. 2002, 124, 9038-9039;
20. b) R. J. Trovitch, E. Lobkovsky, P.J. Chirik, Inorg. Chem. 2006, 45, 7252-7260;
21. c) S. M. Kloek, D. M. Heinekey, K. I. Goldberg, Angew. Chem. 2007, 119, 4820-4822;
22. Angew. Chem. Int. Ed. 2007, 46, 4736-4738;
23. d) M. Feller, E. Ben-Ari, T. Gupta, L. J. W. Shimon, G. Leitus, Y. Diskin-Posner, L. Weiner, D. Milstein, Inorg. Chem. 2007, 46, 10479-10490;
24. e) B. M. Cochran, F. E. Michael J. Am. Chem. Soc. 2008, 130, 2786-2792.
25. The DFT calculations were performed at B3LYP/6-31Gd level of theory. Further computational details and the visualization of a range of molecular orbitals of 3 can be found in the Supporting Information for comparison.
26. Gaussian03 (Revision B.05), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara. M. Challacombe. P. M. W. Gill. B. Johnson, W. Chen, M. W. Wong. C. Gonzalez. J. A. Pople, Gaussian. Inc., Pittsburgh, PA, 2003.
27. A. Jouaiti. M. Geoffroy. G. Bernardinelli. Tetrahedron Lett. 1992, 33, 5071.
28. S. Ekici, D. Gudat, M. Nieger, L. Nyulaszi, E. Niecke, Angew. Chem. 2002, 114, 3515-3519;
29. Angew. Chem. Int. Ed. 2002, 41, 3367-3371.
30. J. I. van der Vlugt, E. A. Pidko, D. Vogt, M. Lutz, A. L. Spek, A. Meetsma, Inorg. Chem. 2008, 47, 4442-4444.
31. G. Kickelbick, K. Matyjaszewski, Macromol. Rapid Commun. 1999, 20, 341-346.
32. a) A. Onoda, K. Kawakita, T. Okamura, H. Yamamoto, N. Ueyama, Acta Crystalhogr. E. 2003, 59, m266 m267;
33. b) E. W. Ainscough, A. M. Brodie, S. L. Ingham, J. M. Waters, J. Chem. Soc. Dalton Trans. 1994, 215-220.
34. H. Feng, X.-P. Zhou, T. Wu, D. Li, Y.-O. Yin, S. W. Ng, Inorg. Chim. Acta 2006, 359, 4027-4035.
35. a) E. G Constable, Chem. Soc., Rev. 2007, 36, 246-253;
36. b) E. C. Constable, Adv. Inorg. Chem. 1986, 30, 69.
37. See also: M. T. Reetz, E. Bohres, R. Goddard, M. C. Holthausen, W. Thiel, Chem. Eur. J. 1999, 5, 2101-2108.
38. I center under formation of complex 3.
39. R. G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533-3539.
40. a) A. Moores, N. Mézailles, N. Maigrot, L. Ricard, F. Mathey, P. Le Floch, Eur. J. Inorg. Chem. 2002, 2034-2039;
41. b) P. LeFloch, L. Ricard, F. Mathey, Bull. Soc. Chim. Fr. 1996, 133, 691-696.
42. a) M. Shiotsuka, T. Tanamachi, T. Urakawa, M. Munakata, Y. J. Matsuda, Supramol Chem. 2002, 2, 211-217;
43. b) M. Shiotsuka, Y. Matsuda, Chem. Lett. 1994, 351 -354;
44. c) N. Mézailles, P. Le Floch, K. Waschbüsch, L. Ricard, F. Mathey, C. P. Kubiak, J. Organomet Chem. 1997, 541, 277-283.
45. A. Hayashi, M. Okazaki, F. Ozawa, Organometallics 2007, 26, 5246-5249.