In-depth insight into the electronic and steric effects of phosphine ligands on the mechanism of the R-R reductive elimination from (PR3)2PdR2

Journal of Organometallic Chemistry

Volumn 694, Issue 13, 2009, Pages 2075-2084

  Ariafard, Alireza ^a,b   Yates, Brian F ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF TASMANIA   (Australia)

Author keywords

Density functional theory; Palladium; Reductive elimination

Indexed keywords

ANCILLARY LIGANDS; ANTI BONDINGS; ANTIBONDING INTERACTIONS; BARRIER HEIGHTS; CONTRIBUTING FACTORS; DECOMPOSITION ANALYSIS; ELECTRON DONATIONS; ELECTRONIC EFFECTS; LIGAND SYSTEMS; ORBITAL STABILIZATIONS; ORBITALS; PALLADIUM COMPLEXES; PHOSPHINE LIGANDS; REDUCTIVE ELIMINATION; STABILIZING INTERACTIONS; STERIC EFFECTS; STERIC FACTORS; TRANSITION STATE; TRANSITION STRUCTURES;

ACTIVATION ENERGY; ALKALINITY; BUTADIENE; DENSITY FUNCTIONAL THEORY; ELECTRONS; PALLADIUM; PALLADIUM COMPOUNDS; PHOSPHORUS COMPOUNDS;

LIGANDS;

EID: 65549092626     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.02.011     Document Type: Article

References (67)

1. Milstein D., and Stille J.K. J. Am. Chem. Soc. 100 (1978) 363
2. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508
3. Espinet P., and Echavarren A.M. Angew. Chem., Int. Ed. 43 (2004) 4704
4. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
5. Hiyama T. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim (Chapter 10)
6. Sonogashira K. J. Organomet. Chem. 653 (2002) 46
7. Tywinski R.R. Angew. Chem., Int. Ed. 42 (2003) 1566
8. Tamao K., Sumitani K., and Kumada M. J. Am. Chem. Soc. 94 (1972) 4374
9. Negishi E., and Anastasia L. Chem. Rev. 103 (2003) 1979
10. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
11. Niu S., and Hall M.B. Chem. Rev. 100 (2000) 353
12. Ananikov V.P., Musaev D.G., and Morokuma K. J. Am. Chem. Soc. 124 (2002) 2839
13. McGuinness D.S., Yates B.F., and Cavell K.J. Organometallics 21 (2002) 5408
14. Graham D.C., Cavell K.J., and Yates B.F. Dalton Trans. (2005) 1093
15. Zuidema E., van Leeuwen P.W.N.M., and Bo C. Organometallics 24 (2005) 3703
16. Graham D.C., Cavell K.J., and Yates B.F. Dalton Trans. (2006) 1768
17. Brown J.M., and Cooley N.A. Chem. Rev. 88 (1988) 1031
18. Ananikov V.P., Musaev D.G., and Morokuma K. Organometallics 24 (2005) 715
19. Tatsumi K., Hoffmann R., Yamamoto A., and Stille J.K. Bull. Chem. Soc. Jpn. 54 (1981) 1857
20. Negishi E., Takahashi T., and Akiyoshi K. J. Organomet. Chem. 334 (1987) 181
21. Mann G., Baranano D., Hartwig J.F., Rheingold A.L., and Guzei I.A. J. Am. Chem. Soc. 120 (1998) 9205
22. Mann G., Shelby Q., Roy A.H., and Hartwig J.F. Organometallics 22 (2003) 2775
23. Ozawa F., Ito T., Nakamura Y., and Yamamoto A. Bull. Chem. Soc. Jpn. 54 (1981) 1868
24. Ozawa F., Kurihara K., Yamamob T., and Yamamoto A. Bull. Chem. Soc. Jpn. 58 (1987) 399
25. Gillie A., and Stille J.K. J. Am. Chem. Soc. 102 (1980) 4933
26. Lou M.K., and Stille J.K. J. Am. Chem. Soc. 103 (1981) 4174
27. Moravskiy A., and Stille J.K. J. Am. Chem. Soc. 103 (1981) 4182
28. Komiya S., Abe Y., Yamamoto A., and Yamamoto T. Organometallics 2 (1983) 1466
29. Komiya S., and Shibue A. Organometallics 4 (1985) 684
30. Komiya S., Ozaki S., and Shibue A. J. Chem. Soc., Chem. Commun. (1986) 1555
31. Komiya S., Shibue A., and Ozaki S. J. Organomet. Chem. 319 (1987) C31
32. Braterman P.S., Cross R.J., and Young G.B. J. Chem. Soc., Chem. Commun. (1975) 627
33. Braterman P.S., Cross R.J., and Young G.B. J. Chem. Soc., Dalton Trans. (1976) 1310
34. Braterman P.S., Cross R.J., and Young G.B. J. Chem. Soc., Dalton Trans. (1976) 1306
35. Braterman P.S., Cross R.J., and Young G.B. J. Chem. Soc., Dalton Trans. (1977) 1892
36. Macgregor S.A., Neave G.W., and Smith C. Faraday Discuss. 124 (2003) 111
37. Choueiry D., and Negishi E.-I. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley, New York
38. Ananikov V.P., Musaev D.G., and Morokuma K. Eur. J. Inorg. Chem. (2007) 5390
39. Bartlett K.L., Goldberg K.I., and Borden T. J. Am. Chem. Soc. 122 (2000) 1456
40. Bartlett K.L., Goldberg K.I., and Borden T. Organometallics 20 (2001) 2669
41. Frenking G., Wichmann K., Fröhlich N., Grobe J., Golla W., Le Van D., Krebs B., and Läge M. Organometallics 21 (2002) 2921
42. Nemcsok D.S., Kovács A., Rayon V.M., and Frenking G. Organometallics 21 (2002) 5803
43. Ariafard A. J. Organomet. Chem. 689 (2004) 2275
44. Fazaeli R., Ariafard A., Jamshidi S., Tabatabaie E.S., and Pishro K.A. J. Organomet. Chem. 692 (2007) 3984
45. M.J. Frisch et al., gaussian 03, Revision B.05, gaussian, Inc., Pittsburgh, PA, 2003.
46. Lee C.T., Yang W.T., and Parr R.G. Phys. Rev. B 37 (1988) 785
47. Becke A.D. J. Chem. Phys. 98 (1993) 5648
48. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200
49. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 270
50. Wadt W.R., and Hay P.J.J. Chem. Phys. 82 (1985) 284
51. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 299
52. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
53. Hgllwarth A., Biihme M., Dapprich S., Ehlers A.W., Gobbi A., Jonas V., Kijhler F., Stegmann R., Veldkamp A., and Frenking G. Chem. Phys. Lett. 208 (1993) 237
54. E.D. Glendening, A.E. Read, J.E. Carpenter, F. Weinhold, NBO (Version 3.1), gaussian, Inc., Pittsburgh, PA, 2003.
55. Tamura H., Yamasaki H., Sato H., and Sakaki S. J. Am. Chem. Soc. 125 (2003) 16114
56. Sumimoto M., Iwane N., Takahama T., and Sakaki S. J. Am. Chem. Soc. 126 (2004) 10457
57. Sakaki S., Takayama T., Sumimoto M., and Sugimoto M. J. Am. Chem. Soc. 126 (2004) 3332
58. Braga A.A.C., Ujaque G., and Maseras F. Organometallics 25 (2006) 3647
59. Kelly E., Seth M., and Ziegler T. J. Phys. Chem. A 108 (2004) 2167
60. Ziegler T., Vanka K., and Xu Z.C.R. Chimie 8 (2005) 1552
61. Yang S.-Y., Szabo M.J., Michalak A., Weiss T., Piers W.E., Jordan R.F., and Ziegler T. Organometallics 24 (2005) 1242
62. Ziegler T., and Rauk A. Theor. Chim. Acta 46 (1977) 1
63. Bickelhaupt F.M. J. Comput. Chem. 20 (1999) 114
64. Diefenbach A., and Bickelhaupt F.M. J. Phys. Chem. A 108 (2004) 8640
65. Diefenbach A., de Jong G.T., and Bickelhaupt F.M. J. Chem. Theor. Comput. 1 (2005) 286
66. In a study like this on interaction and binding energies, basis set super position error (BSSE) could be an issue. To alleviate this concern we have recalculated the energy decomposition data given in Tables 1 and 2 using larger basis sets. These results are listed in Tables S1 and S2 in Supplementary material. These results show little changes and imply that the standard basis set (BS1) is reliable enough to be used for the energy decomposition analysis.
67. Ariafard A., and Lin Z. Organometallics 25 (2006) 4030