Migratory insertion of allyl groups across the Pd-C bond in palladium(ii) isocyanide complexes. the fundamental interplay between temperature and allyl hapticity

Organometallics

Volumn 28, Issue 23, 2009, Pages 6762-6770

  Canovese, Luciano ^a   Visentin, Fabiano ^a   Santo, Claudio ^a   Levi, Carlo ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL FRAGMENTS; ALLYL GROUPS; CHLORINATED SOLVENT; HAPTICITIES; INSERTION PROCESS; INSERTION PRODUCTS; ISOCYANIDES; MIGRATORY INSERTION; THERMODYNAMIC PARAMETER;

CHLORINE COMPOUNDS; CYANIDES; EQUILIBRIUM CONSTANTS; FLUORINE CONTAINING POLYMERS; OLIGOMERS; PALLADIUM; RATE CONSTANTS; TECHNOLOGICAL FORECASTING; TEMPERATURE INDICATING CAMERAS;

PALLADIUM COMPOUNDS;

EID: 71949099284     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900786e     Document Type: Article

References (55)

1. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173-1192.
2. (b) Godlesky, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelbach M. F., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 4, p 585.
3. (c) Tsuji, J. In Palladium and Catalysts Innovation in Organic Synthesis; Wiley: Chichester, U.K. 1995; p 290.
4. (d) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
5. (e) M et al-catalyzed Cross-coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
6. (a) Trost, B. M.; Keinam, E. J. Am. Chem. Soc. 1978, 100, 7779-7781.
7. (b)Trost, B. M.; Verhoeven, T. B. J. Am. Chem. Soc. 1980, 102, 4730-4743.
8. (c) Granberg, K. L.; Bäckvall, J. E. J. Am. Chem. Soc. 1992, 114, 6858-6863.
9. (a) Jutand, A. Appl. Organomet. Chem. 2004, 18, 574-582, and references therein.
10. (b) Garcia-Iglesias, M.; Buñuel, E.; Cárdenas, D. J. Organometallics 2006, 25, 3611-3618, and references therein.
11. (c) Aydin, J.; Szabó K. J. Org. Lett. 2008, 10, 2881-2884, and references therein.
12. Cucciolito, M. E.; Vitagliano, A. Organometallics 2008, 27, 6360-6363.
13. Crociani, B. In Reactions of Coordinated Ligands; Plenum: New York, Vol.1, 1982; p 553, and references therein.
14. (a) Dupont, J.; Pffefer, M.; Daran, J. C.; Jeannin, Y. Organometallics 1987, 6, 899-901.
15. (b) Zografidis, A.; Polborn, K.; Beck, W.; Markies, B. A.; van Koten, G. Z. Naturforsch., B: Chem. Sci. 1994, 49, 1494-1498.
16. (c) Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433-446.
17. (d) Kayaki, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1997, 70, 917-927.
18. (e) Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Speck, A. L.; van Neer, F. J. R. Organometallics 1997, 16, 2948-2957.
19. (f) Vicente, J.; Abad, J. A.; Shaw, K. F.; Gil-Rubio, J.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 1997, 16, 4557-4566.
20. (g) Böhm, A.; Polborn, K.; Sünkel, K.; Beck, W. Z. Naturforsch., B: Chem. Sci. 1998, 53, 448-458.
21. (h) Lin, Y.-S.; Yamamoto, A. Organometallics 1998, 17, 3466-3478.
22. (i) Vicente, J.; Saura-Llamas, I.; Turpin, J.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 1999, 18, 2683-2693.
23. (j) Yamamoto, A. J. Chem. Soc., Dalton Trans. 1999, 1027-1038.
24. (k) Saluste, C.G.; Whitby, R. J.;Furber, M. Angew. Chem., Int.Ed. 2000, 59, 4156-4158.
25. (l)Vicente, J.; Abad, J. A.; Frankland, A. D.; Lopez-Serrano, J.; Ramirez de Arellano, M. C.; Jones, P. G. Organometallics 2002, 21, 272-282.
26. (m) Onitsuka, K.; Yamamoto, M.; Suzuki, S.; Takahashi, S. Organometallics 2002, 21, 581-583.
27. (n) Vicente, J.; Abad, J.-A.; Martinez-Viviente, E.; Jones, P. G. Organometallics 2002, 21, 4454-4467.
28. (o) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215-3218.
29. (p) Kim, Y. J.; Chang, X. H.; Han, J. T.; Lim, M. S.; Lee, S. W. Dalton Trans. 2004, 3699-3708.
30. (q) Albert, J.; D'Andrea, L.; Granell, J.; Zafrilla, J.; Font-Bardia, M.; Solans, X. J. Organomet. Chem. 2007, 692, 4895-4902.
31. (r) Canovese, L.; Visentin, F.; Santo, C.; Levi, C.; Dolmella, A. Organometallics 2007, 26, 5590-5601.
32. (s) Bortoluzzi, M.; Paolucci, G.; Pitteri, B.; Vavasori, A.; Bertolasi, V. Organometallics 2009, 28, 3247-3255.
33. Zhang, J.; Braunstein, P.; Welter, R. Inorg. Chem. 2004, 43, 4172-4177, and references therein.
34. (a) Kajimoto, T; Takahashi, H.; Tsuji, J. J. Organomet. Chem. 1970, 23, 275-280.
35. (b) Boschi, T.; Crociani, B. Inorg. Chim. Acta 1971, 5, 477-480.
36. (c) Scrivanti, A.; Carturan, G.; Crociani, B. Organometallics 1983, 2, 1612-1617.
37. Gambino, G. "Thesis", Università Ca' Foscari, Venice, 2006.
38. Canovese, L.; Visentin, F.; Uguagliati, P.; Bandoli, G. Inorg. Chim. Acta 1988, 277, 247-252.
39. In Scheme 2 the complex MD2Cl should display a cis structure according to the theory of the nucleophilic substitution in square-planar complexes, which states that any substitution occurs with retention of the initial configuration. We, however, cannot exclude that in the presence of free nucleophile such as chloride and/or DIC an extensive cis-trans isomerization takes place, as the spectra seem to indicate.
40. The presence of chloride as counterion of the complex MD2 induces the formation of the MD2Cl derivative at any concentration.
41. Canovese, L.; Visentin, F.; Uguagliati, P.; Chessa, G.; Pesce, A. J. Organomet. Chem. 1998, 566, 61-71.
42. 1H NMR technique.
43. (a) Rülke, R. E.; Kliphuis, D.; Elsevier, C. J.; Fraanje, J.; Goubitz, K.; van Leeuwen, P. W. N. M.; Vrieze, K. J. Chem. Soc., Chem. Commun. 1994, 1817-1819.
44. (b) Wehman, P.; Rülke, R. E.; Kaasjager, V. E.; Kamer, P. C. J.; Kooijman, H.; Spek, A. L.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M., J. Chem. Soc., Chem. Commun. 1995, 331-332.
45. (c) Rülke, R. E; Kaasjager, V. E.; Vehman, P.; Elsevier, C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Fraanje, J.; Goubitz, K.; Spek, A. L. Organometallics 1996, 15, 3022-3031.
46. (d) Byers, P. K.; Canty, A. J. J. Chem. Soc., Chem. Commun. 1988, 639-641.
47. (e) Ramdeehul, S.; Barloy, L.; Osborn, J. A.; De Cian, A.; Fisher, J. Organometallics 1996, 15, 5442-5444.
48. (f) Barloy, L.; Ramdeehul, S.; Osborn, J. A.; Carlotti, C.; Taulelle, F.; De Cian, A.; Fisher, J. Eur. J. Inorg. Chem. 2000, 2523-2532.
49. (a) Braunstein, P.; Naud, F.; Dedieu, A.; Rohmer, M.-M.; DeCian, A.; Rettig, S. J. Organometallics 2001, 20, 2966-2981.
50. (b) Kolmar, M.; Helmchen, G. Organometallics 2002, 21, 4771-4775.
51. (c) Braunstein, P.; Zhang, J.; Welter, R. J. Chem. Soc., Dalton Trans. 2003, 507-509.
52. 1-allyl complex bearing the chloride ion coordinated together with the potentially tris-chelating bis(oxazoline) acting as a bischelating ligand was observed.
53. Mesnager, J.; Kuntz, E.; Pinel, C. J. Organomet. Chem. 2009, 594, 2513-2518.
54. Hartley, F. R.; Jones, S. R. J. Organomet. Chem. 1974, 66, 465-473.
55. Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046.