Theoretical studies of the oxidative addition of PhBr to Pd(PX3)2 and Pd(X2PCH2CH2PX2) (X = Me, H, Cl)

Journal of Organometallic Chemistry

Volumn 692, Issue 18, 2007, Pages 3984-3993

  Fazaeli, Reza ^a   Ariafard, Alireza ^b   Jamshidi, Saiedeh ^b   Tabatabaie, Elham S ^b,c   Pishro, Khatereh A ^c  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b Department of Chemistry   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Density functional theory calculations; Oxidative addition; Palladium

Indexed keywords

ACTIVATION ENERGY; ADDITION REACTIONS; BOND STRENGTH (CHEMICAL); DENSITY FUNCTIONAL THEORY; LIGANDS; OXIDATION; RIGIDITY;

DENSITY FUNCTIONAL THEORY CALCULATIONS; ORBITAL ENERGY; OXIDATIVE ADDITION; PHOSPHINE;

PALLADIUM;

EID: 34547093220     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2007.06.011     Document Type: Article

References (70)

1. Espinet P., and Echavarren A.M. Angew. Chem., Int. Ed. Engl. 43 (2004) 4704
2. Beletskaya I.P., and Cheprakov A.V. Chem. Rev. 100 (2000) 3009
3. Crisp G.T. Chem. Soc. Rev. 27 (1998) 427
4. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
5. de Meijere A., and Meyer F.E. Angew. Chem., Int. Ed. Engl. 33 (1994) 2379
6. Stille J.K. Angew. Chem. Int. Ed. 25 (1986) 508
7. Christmann U., and Vilar R. Angew. Chem. Int. Ed. 44 (2005) 366
8. Beeby A., Bettington S., Fairlamb I.J.S., Goeta A.E., Kapdi A.R., and Thompson A.L. New J. Chem. 28 (2004) 600
9. Tsuji J. Palladium Reagents and Catalysts (2004), Wiley
10. Diederich F., and Stang P.J. Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim
11. Sundermann A., and Martin J.M.L. Chem. Eur. J. 7 (2001) 1703
12. Barrios-Landeros F., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 6944
13. Roy A.H., and Hartwig J.F. J. Am. Chem. Soc. 125 (2003) 13944
14. Amatore C., and Jutand A. Acc. Chem. Res. 33 (2000) 314
15. Amatore C., and Jutand A. J. Organomet. Chem. 576 (1999) 254
16. Casado A.L., and Espinet P. Organometallics 17 (1998) 954
17. Jutand A., and Mosleh A. Organometallics 14 (1995) 1810
18. Hartwig J.F., and Paul F. J. Am. Chem. Soc. 117 (1995) 5373
19. Paul F., Patt J., and Hartwig J.F. Organometallics 14 (1995) 3030
20. Amatore C., Jutand A., and Suarez A. J. Am. Chem. Soc. 115 (1993) 9531
21. Portnoy M., and Milstein D. Organometallics 12 (1993) 1665
22. Amatore C., and Pflüger F. Organometallics 9 (1990) 2276
23. Ahlquist M., Fristrup P., Tanner D., and Norrby P.-O. Organometallics 25 (2006) 2066
24. Kozuch S., Amatore C., Jutand A., and Shaik S. Organometallics 24 (2005) 2319
25. Goossen L.J., Koley D., Hermann H.L., and Thiel W. Organometallics 24 (2005) 2398
26. Goossen L.J., Koley D., Hermann H.L., and Thiel W. Chem. Commun. (2004) 2141
27. Ariafard A., and Lin Z. Organometallics 25 (2006) 4030
28. Diefenbach A., de Jong G.T., and Bickelhaupt F.M. J. Chem. Theory Comput. 1 (2005) 286
29. Senn H.M., and Ziegler T. Organometallics 23 (2004) 2980
30. Jakt M., Johannissen L., Rzepa H.S., Widdowson D.A., and Wilhelm A. J. Chem. Soc., Perkin Trans. 2 (2002) 576
31. Albert K., Gisdakis P., and Rösch N. Organometallics 17 (1998) 1608
32. Bickelhaupt F.M., Ziegler T., and Schleyer P.v.R. Organometallics 14 (1995) 2288
33. Ahlquist M., and Norrby P.-O. Organometallics 26 (2007) 550
34. Lam K.C., Marder T.B., and Lin Z. Organometallics 26 (2007) 758
35. Braga A.A.C., Ujaque G., and Maseras F. Organometallics 25 (2006) 3647
36. Cundari T.R., and Deng J. J. Phys. Org. Chem. 18 (2005) 417
37. Ariafard A. J. Organomet. Chem. 689 (2004) 2275
38. Frenking G., Wichmann K., Fröhlich N., Grobe J., Golla W., Le Van D., Krebs B., and Läge M. Organometallics 21 (2002) 2921
39. Nemcsok D.S., Kovács A., Rayon V.M., and Frenking G. Organometallics 21 (2002) 5803
40. Crabtree R.H. The Organometallic Chemistry of the Transition Metals. fourth ed. (2005), Wiley, New York pp. 101-102
41. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski Jr. V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M.C.R., Mennucci B., Pomelli C., Adamo C., Cliord S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. gaussian 98 Revision A.7 (1998), Gaussian, Inc., Pittsburgh, PA
42. Becke A.D. J. Chem. Phys. 98 (1993) 5648
43. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200
44. Lee C., Yang W., and Parr G. Phys. Rev. B 37 (1988) 785
45. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 270
46. Wadt W.R., and Hay P.J. J. Chem. Phys. 82 (1985) 284
47. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 299
48. Hariharan P.C., and Pople J.A. Theor. Chim. Acta 28 (1973) 213
49. Huzinaga S. Gaussian Basis Sets for Molecular Calculations (1984), Elsevier, Amsterdam/New York p. 70
50. Glendening E.D., Read A.E., Carpenter J.E., and Weinhold F. NBO (version 3.1) (1998), Gaussian, Inc., Pittsburg, PA
51. Ehlers A.W., Bohme M., Dapprich S., Gobbi A., Hollwarth A., Jonas V., Kohler K.F., Stegmann R., Veldkamp A., and Frenking G. Chem. Phys. Lett. 208 (1993) 111
52. Bergner A., Dolg M., Kuechle W., Stoll H., and Preuss H. Mol. Phys. 80 (1993) 1431
53. Dolg M., Wedig U., Stoll H., and Preuss H. J. Chem. Phys. 86 (1987) 866
54. Dapprich S., and Frenking G. J. Phys. Chem. 99 (1995) 9352
55. S. Dapprich, G. Frenking, CDA 2.1, Marburg, Germany, 1994.
56. 3 groups cannot play a crucial role in the reactivity.
57. Diefenbach A., de Jong G.T., and Bickelhaupt F.M. J. Chem. Theory Comput. 1 (2005) 286
58. Diefenbach A., and Bickelhaupt F.M. J. Phys. Chem. A 108 (2004) 8640
59. Bickelhaupt F.M. J. Comput. Chem. 20 (1999) 114
60. Urata H., Tanaka M., and Fuchikami T. Chem. Lett. (1987) 751
61. Boehme C., and Frenking G. Organometallics 17 (1998) 5801
62. Uddin J., Dapprich S., Frenking G., and Yates B.F. Organometallics 18 (1999) 457
63. Corbet J.-P., and Mignani G. Chem. Rev. 106 (2006) 2651
64. Su M.-D., and Chu S.-Y. Chem. Phys. Lett. 282 (1998) 25
65. Yammamoto A., Yammamoto T., and Ozawa F. Pure Appl. Chem. 57 (1985) 1799
66. Matsubara T. Organometallics 22 (2003) 4286
67. McGuinness D.S., Cavell K.J., Yates B.F., Skelton B.W., and White A.H. J. Am. Chem. Soc. 123 (2001) 8317
68. Su M.-D., and Chu S.-Y. Inorg. Chem. 37 (1998) 3400
69. Sakaki S., Biswas B., and Sugimoto M. J. Chem. Soc., Dalton Trans. (1997) 803
70. Portnoy M., and Milstein D. Organometallics 12 (1993) 1665