Insertion of isocyanides across the Pd-C bond in alkyl or aryl palladium(II) complexes bearing mixed nitrogen-sulfur and nitrogen-phosphorus ancillary ligands. The mechanism of reaction

Organometallics

Volumn 26, Issue 23, 2007, Pages 5590-5601

  Canovese, Luciano ^a   Visentin, Fabiano ^a   Santo, Claudio ^a   Levi, Carlo ^a   Dolmella, Alessandro ^b  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; LIGANDS; NITROGEN COMPOUNDS; REACTION KINETICS; SULFUR COMPOUNDS;

ISOCYANIDES; MIXED NITROGEN-SULFUR; NITROGEN-PHOSPHORUS ANCILLARY LIGANDS; TOSYLMETHYL ISOCYANIDE (TOSMIC);

PALLADIUM COMPOUNDS;

EID: 36249014967     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700555a     Document Type: Article

References (72)

1. Heck, R. F. In Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
2. Tsuji, J. In Palladium Reagents and Catalysts; John Wiley: Chichester, U.K., 1995.
3. Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Santo, C.; Dolmella, A. Organometallics 2005, 24, 3297, and references therein (for structural comparison entry codes PAQPED, PAQPIH).
4. Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Speck, A. L. Organometallics 1997, 16, 4150.
5. (a) Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Santo, C.; Bandoli, G.; Maini, L. Organometallics 2003, 22, 3230, and references therein.
6. (b) Groen, J. H.; Delis, J. G. P.; van Leeuwen, P. W. N. M.; Vrieze, K. Organometallics 1997, 16, 68.
7. (c) Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Speck, A. L. Organometallics 1997, 16, 2948.
8. (a) Wojcicki, A. A. Adv. Organomet. Chem. 1973, 11, 87.
9. (b) Kulhman, E. J.;. Alexander, J. J. J. Coord. Chem. Rev. 1980, 33, 195.
10. (c) Backer, T. M.; Alexander, J. J.; Krause Bauer J. A.; Nauss, J. L.; Wireko, F. C Organometallics 1999, 18, 663
11. (d) Haore, J. L.; Cavell, K. J.; Hecker, R.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1996, 2197.
12. (e) Koga, N.; Morokuma, K. In Theoretical Aspects of Homogeneous Catalysis; van Leeuwen, P. W. N. M., Morokuma, K., van Lenthe, J. H., Eds.; Kluwer: Dordrecht, The Netherlands, 1995.
13. (f) Calhorda, H. J.; Brown, J. M.; Cooley, N. A. Organometallics 1991, 10, 1431.
14. (g) Margl, P.; Ziegler, T. J. Am. Chem. Soc. 1996, 118, 7337.
15. (a) Veya, P.; Floriani, C. Organometallics 1993, 12, 4899.
16. (b) 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.
17. (c) Owen, G. R.; Vilar, R.; White, A. J. P.; Williams, D. J. Organometallics 2002, 21, 4799.
18. (d) Vicente, J.; Abad, J-A.; Martinez-Viviente, E.; Jones, P. G. Organometallics 2002, 21, 4454, and references therein.
19. (a) Canovese, L.; Visentin, F.; Chessa, G.; Santo, C.; Uguagliati, P.; Bandoli, G. J. Organomet. Chem. 2002, 650, 43, and references therein (for structural comparison entry code HUGGAR).
20. (b) Delis, J. G. P.; Aubel, P. G.; van Leeuwen, P. W. N. M.; Vrieze, K.; Veldman, N.; Speck, A. L. J. Chem. Soc., Chem. Commun. 1995, 2233.
21. (a) Drent, E.; van Broekhoven, J. A. M.; Doyle, M. J. J. Organomet. Chem. 1991, 417, 235.
22. (b) Sen, A.; Jiang, Z. Macromolecules 1993, 26, 911.
23. (c) Brookhart, M.; Wagner, M. I. J. Am. Chem. Soc. 1994, 116, 3641.
24. (d) van Asselt, R.; Gielens, E. E. C. G.; Rülke, R. E.; Vrieze, K.; Elsevier, C. J. J. Am. Chem. Soc. 1994, 116, 977.
25. (e) Markies, B. A.; Kruis, D.; Rietveld, M. H. P.; Verkerk, K. A.; Boersma, J.; Koijman, H.; Lakin, M. T.; Speck, A. L.; van Koten, G. J. Am. Chem. Soc. 1995, 117, 5263.
26. (f) Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 4746.
27. Crociani, B. In Reactions of Coordinated Ligands; Plenum: New York, Vol. 1, 1982; p 553, and references therein.
28. Kayaki, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1997, 70, 917.
29. Canovese, L.; Visentin, F.; Chessa, G.; Uguagliati, P.; Bandoli, G. Organometallics 2000, 19, 1461.
30. (a) Abel, E. W.; Evans, D. G.; Koe, J. R.; Sik, V.; Hursthome, M. B.; Bates, P. A. J. Chem. Soc., Dalton Trans. 1989, 2315.
31. (b) Abel, E. W.; Dormer, J. C.; Ellis, K. J.; Hursthome, M. B.; Mazid, M. A. J. Chem. Soc., Dalton Trans. 1991, 107.
32. Canovese, L.; Lucchini, V.; Santo, C.; Visentin, F.; Zambon, A. J. Organomet. Chem. 2002, 642, 58.
33. Johnson, C. K. ORTEP, Report ORNL-5138; Oak Ridge National Laboratory: Oak Ridge, TN, 1976.
34. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388; Cambridge Structural Database (Version 5.27 of November 2005 + 3 updates).
35. Spencer, J.; Pfeffer, M.; Kyritsakas, N.; Fischer, J. Organometallics 1995, 14, 2214 (entry codes ZAFCUE, ZAFDEP, ZAFDAL).
36. At higher temperature (255 K) traces of the insertion product are observed; however the estimated concentration of the latter is less than 5% of the concentration of the starting complex.
37. Owing to the very large errors affecting the determination of the concentrations, standard errors of the van't Hoff regression are not reported. Therefore, the equilibrium constant values must be considered as rough estimates of their order of magnitude.
38. Annibale, G.; Canovese, L.; Cattalini, L.; Marangoni, G.; Michelon, G.; Tobe, M. L. Inorg. Chem. 1981, 20, 2428.
39. The NSMe species represents the less strongly bonded ligand among all the ligands used in this work. Therefore, its added concentration would represent the limiting concentration also in the case of NSt-Bu (DPPQ and DPPQMe are not displaced by isocyanide).
40. 2 values were determined in the absence of added chloride by numerical regression of the absorbance vs time data according to the second-order treatment. Such values are purely indicative since the treatment is obviously inadequate owing to the complexity of the overall reaction mechanism. Nevertheless, the comparison among rates is warranted by the fairly satisfactory fit obtained.
41. Canovese, L.; Visentin, F.; Chessa, G.; Santo, C.; Uguagliati, P. Inorg. Chim. Acta 2003, 346, 158.
42. Tobe, M. L.; Burgess. J. In Inorganic Reactions Mechanisms; Addison Wesley: New York, 1999.
43. (a) ORTEP-3 for Windows, Version 1.08; University of Glasgow, 2005.
44. (b) Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
45. (a) Henslee, G. W.: Oliver, J. D. J. Cryst. Mol. Struct. 1977, 7, 137 (entry code PZALPD10).
46. (b) Bacchi, A.; Carcelli, M.; Pelagatti, P.; Pelizzi, C.; Pelizzi, G.; Salati, C.; Sgarabotto, P. Inorg. Chim. Acta 1999, 295, 171 (entry code KAMQUK).
47. (c) Wu, W.-S.; Chen, J.: Dai, J.-C.; Lin, J.-M.; Lan, X.-R.; Huang, T.-T. Huaxue Xuebao (Chin.) (Acta Chim. Sinica) 2005, 63, 1967 (entry code WERJAF).
48. (a) Onitsuka, K.; Segawa, M.; Takahashi, S. Organometallics 1998, 17, 4335 (entry code JAQKAN).
49. (b) Braunstein, P.; Durand, J.; Knorr, M.; Strohmann, C. Chem. Commun. 2001, 211 (entry code WOXGAR).
50. (c) Onitsuka, K.; Yamamoto, M.; Suzuki, S.; Takahashi, S. Organometallics 2002, 21, 581 (entry code LOWVAU).
51. (d) Owen, G. R.; Vilar, R.; White, A. J. P.; Williams, D. J. Organometallics 2003, 22, 4511 (entry codes UMEDOF, UMEDUL).
52. (e) Knorr, M.; Jourdain, I.; Braunstein, P.; Strohmann, C.; Tiripicchio, A.; Ugozzoli, F. Dalton Trans. 2006, 5248 (entry code MESZOA).
53. (a) Yamamoto, Y.; Tanase, T.; Yanai. T.; Asano, T.; Kobayashi, K. J. Organomet. Chem. 1993, 456, 287 (entry code LAYPUW).
54. (b) Delis, J. G. P.; Aubel, P. G.; Vrieze, K.; van Leeuwen, P. W. N. M.; Veldman, N.; Spek, A. L. Organometallics 1997, 16, 4150 (entry code NOHCUI).
55. (c) Bianchini, C.; Lee, H.-M.; Mantovani, G.; Meli, A.; Oberhauser, W. New J. Chem. 2002, 26, 387 (entry code XISQIZ).
56. (d) Owen, G. R.; Vilar, R.; White, A. J. P.; Williams, D. J. Organometallics 2003, 22, 3025 (entry code OKAYUU).
57. (e) Lai, Y.-C.; Chen, H.-Y.; Hung, W.-C.; Lin, C.-C.; Hong, F.-E. Tetrahedron 2005, 61, 9484 (entry code GATBOT).
58. (f) Hsueh. M.-L.; Su, S.-Y.; Lin, C.-C. Acta Crystallogr., Sect. E 2006, 62, m1784 (entry code DELRIW).
59. (g) Zhang, W.; Sun, W.-H.; Wu, B.; Zhang, S.; Ma, H.; Li, Y.; Chen, J.; Hao, P. J. Organomet. Chem. 2006, 691, 4759 (entry codes NESHOJ, NESJAX).
60. Spartan '06 for Windows Version 1.1.0: Wavefunction, Inc.: Irvine, CA, 2006.
61. (a) Uson, R.; Forniés, J.; Espinet, P.; Lalinde, E. J. Organomet. Chem. 1988, 349, 269.
62. (b) Uson, R.; Forniés, J.; Espinet, P.; Pueyo, L.; Lalinde, E. J. Organomet. Chem. 1986, 299, 251, and references therein.
63. Dupont, J.; Pfeffer, M.; Daran, J. C.; Jeannin, Y. Organometallics 1987, 6, 899, and references therein.
64. Bertani, R.; Mozzon, M.; Michelin, R. A.; Benetollo, F; Bombieri, G.; Castilho, T. J.; Pombeiro. A. J. L. Inorg. Chim. Acta 1991, 189, 175.
65. Mackay, S.; Gilmore, C. J.; Edwards, C.; Stewart, N.; Shankland, K. maXus, computer program for the solution and refinement of crystal structures; Nonius: The Nederlands, MacScience: Japan, and the Univeristy of Glasgow, 1999.
66. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Gagliardi, A.; Burla, M. C.; Polidori, G.; Cavalli, M. J. Appl. Crystallogr. 1994, 27, 435.
67. Sheldrick, G. M. SHELXTL NT, Version 5.10; Bruker AXS Inc.: Madison, WI, 1999.
68. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1997.
69. Canovese, L.; Visentin, F.; Uguagliati, P.; Chessa, G.; Pesce, A. J. Organomet. Chem. 1998, 566, 61.
70. (38)Wehman, P.; van Donge, H. M. A.; Hagos, A.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Organomet. Chem. 1997, 535, 183.
71. Rudler-Chavin, M.; Rudler, H. J. Organomet. Chem. 1977, 134, 15.
72. Alsters, P. L.; Boersma, J.; van Koten, G. Organometallics 1993, 12, 1629.