Theoretical insight into the C-C coupling reactions of the vinyl, phenyl, ethynyl, and methyl complexes of palladium and platinum

Organometallics

Volumn 24, Issue 4, 2005, Pages 715-723

  Ananikov, Valentine P ^a,b   Musaev, Djamaladdin G ^b   Morokuma, Keiji ^b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIER; BOND DISSOCIATION ENERGY (BDE); EXOTHERMICITY; LIGANDS;

CATALYSIS; CHEMICAL BONDS; COMPLEXATION; DISSOCIATION; MOLECULAR STRUCTURE; PALLADIUM; PLATINUM; THERMODYNAMICS;

REACTION KINETICS;

EID: 14544296576     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0490841     Document Type: Article

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26. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
27. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
28. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
29. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
30. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
31. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
32. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
33. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
34. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
35. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
36. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
37. For representative studies see: (a) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857. (b) Low, J. L.; Goddard, W. A. J. Am. Chem. Soc. 1986, 108, 6115. (c) Low, J. L.; Goddard, W. A. Organometallics 1986, 5, 609. (d) Koga, N.; Morokuma, K. Organometallics 1991, 10, 946. (e) Blomberg, M. R. A., Siegbahn, P. E. M.; Nagashina, U.; Wennerberg, J. J. Am. Chem. Soc. 1991, 113, 424. (f) Siegbahn, P. E. M.; Blomberg, M. R. A. J. Am. Chem. Soc. 1992, 114, 10548. (g) Sakaki, S.; Ieki, M. J. Am. Chem. Soc. 1993, 115, 2373. (h) Sakaki, S.; Ogawa, M.; Musashi, Y.; Arai, T. Inorg. Chem. 1994, 33, 1660. (i) Sakaki, S.; Mizoe, N.; Musashi, Y.; Biswas, B.; Sugimoto, M. J. Phys. Chem. A 1998, 102, 8027. (j) Hill, G. S.; Puddephatt, R. J. Organometallics 1998, 17, 1478. (k) Cao, Z.; Hall, M. B. Organometallics 2000, 19, 3338. (l) Sundermann, A.; Uzan, O.; Milstein, D.; Martin, J. M. L. J. Am. Chem. Soc. 2000, 122, 7095. (m) Sundermann, A.; Uzan, O.; Martin, J. M. L. Organometallics 2001, 20, 1783.
38. For general reviews see: (a) Didieu, A. Chem. Rev. 2000, 100, 543. (b) Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107. (c) Siegbahn, P. E. M.; Blomberg, M. R. A. In Theoretical Aspects of Homogeneous Catalysis, Applications of Ab Initio Molecular Orbital Theory; van Leeuwen, P. W. N. M., van Lenthe, J. H., Morokuma, K., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 1995. (d) Koga, N.; Morokuma, K. Chem. Rev. 1991, 91, 823.
39. For general reviews see: (a) Didieu, A. Chem. Rev. 2000, 100, 543. (b) Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107. (c) Siegbahn, P. E. M.; Blomberg, M. R. A. In Theoretical Aspects of Homogeneous Catalysis, Applications of Ab Initio Molecular Orbital Theory; van Leeuwen, P. W. N. M., van Lenthe, J. H., Morokuma, K., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 1995. (d) Koga, N.; Morokuma, K. Chem. Rev. 1991, 91, 823.
40. For general reviews see: (a) Didieu, A. Chem. Rev. 2000, 100, 543. (b) Musaev, D. G.; Morokuma, K. Top. Catal. 1999, 7, 107. (c) Siegbahn, P. E. M.; Blomberg, M. R. A. In Theoretical Aspects of Homogeneous Catalysis, Applications of Ab Initio Molecular Orbital Theory; van Leeuwen, P. W. N. M., van Lenthe, J. H., Morokuma, K., Eds.; Kluwer Academic: Dordrecht, The Netherlands, 1995. (d) Koga, N.; Morokuma, K. Chem. Rev. 1991, 91, 823.
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69. 2 complex as being more energetically favored. See examples of different complexes and dissociation transition states in Figure S6.
70. During the constrained optimization the value of a was frozen and the square-planar geometry of the metal complex was maintained. All the other geometry parameters were optimized.
71. For a graphical representation, see Scheme 2 and Figure S4.
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