Formation of fluorinated platinum-stilbazole complexes: Aryl-halide oxidative addition vs η2-coordination of a carbon-carbon double bond

Organometallics

Volumn 25, Issue 14, 2006, Pages 3308-3310

  Lucassen, André C B ^a   Shimon, Linda J W ^a   Van Der Boom, Milko E ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CHEMICAL BONDS; COMPLEXATION; FLUOROCARBONS; ORGANIC COMPOUNDS; OXIDATION; REACTION KINETICS; THERMODYNAMIC PROPERTIES;

ARYL-HALIDE OXIDATIVE ADDITION; FLUORINATED STILBAZOLE LIGAND; ISOSTRUCTURAL SYSTEMS; ZEROVALENT PLATINUM COMPLEXES;

PLATINUM COMPOUNDS;

EID: 33746655801     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0603870     Document Type: Article

References (36)

1. For reviews, see: (a) Zapf, A.; Beller, M. Chem. Commun. 2005, 4, 431.
2. (b) Slagt, M. Q.; van Zwieten, D. A. P.; Moerkerk, A. J. C. M.; Gebbink, R. J. M. L.; van Koten, G. Coord. Chem. Rev. 2004, 248, 2275.
3. (c) Espinet, P.; Echavarren, M. Angew. Chem., Int. Ed. 2004, 43, 4704.
4. (d) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
5. (e) Elsevier, C. J. Coord. Chem. Rev. 1999, 185-186, 809.
6. Negishi, E. I. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley: New York, 2002.
7. Diederich, F.; Stang, P. J. Metal-catalyzed Cross-Coupling Reactions; Wiley-VCH: New York, 1998.
8. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 1st ed.; University Science Books: Mill Valley, CA, 1994.
9. For some recent studies, see: (a) Gatard, S.; Celenligil-Cetin, R.; Guo, C.; Foxman, B. M.; Ozerov, O. V. J. Am. Chem. Soc. 2006, 128, 2808.
10. (b) Fan, L.; Parkin, S.; Ozerov, O. V. J. Am. Chem. Soc. 2005, 127, 16772.
11. (c) Dong, C.-G.; Hu, Q.-S. J. Am. Chem. Soc. 2005, 127, 10006.
12. (d) Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944.
13. (e) Ben-Ari, E.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2003, 125, 4714.
14. (f) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
15. (g) For catalytic functionalization of perfluoroarenes by the Heck reaction: Albeniz, A. C.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504.
16. (h) For a theoretical study: Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2398.
17. Strawser, D.; Karton, A.; Zenkina, O. V.; Iron, M. A.; Shimon, L. J. W.; Martin, J. M. L.; van der Boom, M. E. J. Am. Chem. Soc. 2005, 127, 9322.
18. Lucassen, A. C. B.; Vartanian, M.; Leitus, G.; van der Boom, M. E. Cryst. Growth Des. 2005, 5, 1671.
19. Schunn, R. A. Inorg. Chem. 1976, 15, 208.
20. See Supporting Information for complete experimental details and characterization data for complexes 2, 4, and 6. The crystal structures of complexes 2 and 6 have been deposited at the Cambridge Crystallographic Data Center and allocated the deposition numbers CCDC 271980 and CCDC 271981, respectively. These data can be obtained free of charge at www.ccdc.cam.ac.uk/ conts/retrieving.html.
21. -3. Note: There is a partially disordered hexane solvent molecule, which has been modeled with only the carbon atoms.
22. (a) Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2117.
23. (b) Usón, R.; Royo, P.; Gimeno, J. J. Organomet, Chem. 1974, 72, 299.
24. 3 in dry THF with the exclusion of light.
25. Gerlach, D. H.; Kane, A. R.; Parshall, G. W.; Jesson, J. P.; Muetterties, E. L. J. Am. Chem. Soc. 1971, 93, 3543.
26. Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1980, 776.
27. Aryl-halide oxidative addition via the intermediacy of 12-electron species: (a) Stambuli, J. P.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346.
28. (b) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
29. (c) For a theoretical study: Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P.-O. Organometallics 2006, 25, 2066.
30. -3.
31. Lorance, E. D.; Kramer, W. H.; Gould, I. R. J. Am. Chem. Soc. 2002, 124, 15225.
32. For a recent study, see: Popp, B. V.; Thorman, J. L.; Morales, C. M.; Landis, C. R.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 14832.
33. (a) Baraban, J. M.; McGinnety, J. A. Inorg. Chem. 1974, 13, 2864.
34. (b) Chatt, J.; Shaw, B. L.; Williams, A. A. J. Chem. Soc. 1962, 3269.
35. For a review, see: Keane, J. M.; Harman, W. D. Organometallics 2005, 24, 1786.
36. 0, see: Whitesides, G. M.; Hackett, M. J. Am. Chem. Soc. 1988, 110, 1449.