-
1
-
-
33947091124
-
-
(a) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
-
(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 4374
-
-
Tamao, K.1
Sumitani, K.2
Kumada, M.3
-
12
-
-
84962385341
-
-
(a) Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 10457
-
-
Sumimoto, M.1
Iwane, N.2
Takahama, T.3
Sakaki, S.4
-
13
-
-
21244496290
-
-
(b) Braga, A. A. C.; Morgon, N. H.; Ujaque, G.; Maseras, F. J. Am. Chem. Soc. 2005, 127, 9298.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 9298
-
-
Braga, A.A.C.1
Morgon, N.H.2
Ujaque, G.3
Maseras, F.4
-
14
-
-
23744446576
-
-
(c) Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. J. Am. Chem. Soc. 2005, 127, 11102.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 11102
-
-
Goossen, L.J.1
Koley, D.2
Hermann, H.L.3
Thiel, W.4
-
15
-
-
84962429991
-
-
(d) Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647.
-
(2006)
Organometallics
, vol.25
, pp. 3647
-
-
Braga, A.A.C.1
Ujaque, G.2
Maseras, F.3
-
17
-
-
48749133648
-
-
(f) Henriksen, S. T.; Norrby, P.-O.; Kaukoranta, P.; Andersson, P. G. J. Am. Chem. Soc. 2008, 130, 10414.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 10414
-
-
Henriksen, S.T.1
Norrby, P.-O.2
Kaukoranta, P.3
Andersson, P.G.4
-
18
-
-
41549151512
-
-
(g) Surawatanawong, P.; Fan, Y.; Hall, M. B. J. Organomet. Chem. 2008, 693, 1552.
-
(2008)
J. Organomet. Chem.
, vol.693
, pp. 1552
-
-
Surawatanawong, P.1
Fan, Y.2
Hall, M.B.3
-
19
-
-
0346265937
-
-
Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 12.v
-
(a) Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol.12.v
-
(1995)
Comprehensive Organometallic Chemistry II
-
-
Farina, V.1
-
20
-
-
0003397781
-
-
Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York
-
(b) Mitchell, T. N. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
-
(1998)
Metal-catalyzed Cross-coupling Reactions
-
-
Mitchell, T.N.1
-
25
-
-
4644245555
-
-
Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 4704
-
-
Espinet, P.1
Echavarren, A.M.2
-
28
-
-
0034614060
-
-
(b) Casado, A. L.; Espinet, P. J.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 11771
-
-
Casado, A.L.1
Espinet, P.J.2
Gallego, A.M.3
-
29
-
-
0242432588
-
-
(c) Casares, J. A.; Espinet, P.; Salas, G. Chem. - Eur. J. 2002, 8, 4844.
-
(2002)
Chem. - Eur. J.
, vol.8
, pp. 4844
-
-
Casares, J.A.1
Espinet, P.2
Salas, G.3
-
30
-
-
33644986119
-
-
(d) Nilsson, P.; Puxty, G.; Wendt, O. F. Organometallics 2006, 25, 1285.
-
(2006)
Organometallics
, vol.25
, pp. 1285
-
-
Nilsson, P.1
Puxty, G.2
Wendt, O.F.3
-
31
-
-
34547093393
-
-
(e) Santos, L. S.; Rosso, G. B.; Pilli, R. A.; Eberlin, M. N. J. Org. Chem. 2007, 72, 5809.
-
(2007)
J. Org. Chem.
, vol.72
, pp. 5809
-
-
Santos, L.S.1
Rosso, G.B.2
Pilli, R.A.3
Eberlin, M.N.4
-
32
-
-
49449099994
-
-
(f) Pérez-Temprano, M. H.; Nova, A.; Casares, J. A.; Espinet, P. J. Am. Chem. Soc. 2008, 130, 10518.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 10518
-
-
Pérez-Temprano, M.H.1
Nova, A.2
Casares, J.A.3
Espinet, P.4
-
33
-
-
0141939530
-
-
(a) Napolitano, E.; Farina, V.; Persico, M. Organometallics 2003, 22, 4030.
-
(2003)
Organometallics
, vol.22
, pp. 4030
-
-
Napolitano, E.1
Farina, V.2
Persico, M.3
-
34
-
-
30944444640
-
-
(b) Álvarez, R.; Faza, O. N.; Lopez, C. S.; de Lera, A. R. Org. Lett. 2006, 8, 35.
-
(2006)
Org. Lett.
, vol.8
, pp. 35
-
-
Álvarez, R.1
Faza, O.N.2
Lopez, C.S.3
De Lera, A.R.4
-
35
-
-
33845305816
-
-
(c) Ariafard, A.; Lin, Z.; Fairlamb, J. S. Organometallics 2006, 27, 5788.
-
(2006)
Organometallics
, vol.27
, pp. 5788
-
-
Ariafard, A.1
Lin, Z.2
Fairlamb, J.S.3
-
36
-
-
33750988497
-
-
(d) Nova, A.; Ujaque, G.; Maseras, F.; Lledos, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 14571
-
-
Nova, A.1
Ujaque, G.2
Maseras, F.3
Lledos, A.4
Espinet, P.5
-
37
-
-
34547199604
-
-
(e) Álvarez, R.; Faza, O. N.; de Lera, A. R.; Cardenas, D. J. Adv. Synth. Catal. 2007, 349, 887.
-
(2007)
Adv. Synth. Catal.
, vol.349
, pp. 887
-
-
Álvarez, R.1
Faza, O.N.2
De Lera, A.R.3
Cardenas, D.J.4
-
38
-
-
49349105775
-
-
(f) Álvarez, R.; Pérez, M.; Faza, O. N.; de Lera, A. R. Organometallics 2008, 27, 3378.
-
(2008)
Organometallics
, vol.27
, pp. 3378
-
-
Álvarez, R.1
Pérez, M.2
Faza, O.N.3
De Lera, A.R.4
-
39
-
-
0001455450
-
-
3)2Pd(Ar)(X) is formed first and then the cis-isomer isomerizes to the thermodynamically more stable trans-isomer (see Scheme 1).
-
3)2Pd(Ar)(X) is formed first and then the cis-isomer isomerizes to the thermodynamically more stable trans-isomer (see Scheme 1). Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954.
-
(1998)
Organometallics
, vol.17
, pp. 954
-
-
Casado, A.L.1
Espinet, P.2
-
40
-
-
0033549832
-
-
(a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2411
-
-
Littke, A.F.1
Fu, G.C.2
-
41
-
-
0037024173
-
-
(b) Littke, A. F.; Schwarz, L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 6343.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 6343
-
-
Littke, A.F.1
Schwarz, L.2
Fu, G.C.3
-
46
-
-
0345491105
-
-
Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.T.1
Yang, W.T.2
Parr, R.G.3
-
48
-
-
0038596731
-
-
Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
-
(1989)
Chem. Phys. Lett.
, vol.157
, pp. 200
-
-
Miehlich, B.1
Savin, A.2
Stoll, H.3
Preuss, H.4
-
53
-
-
43949164303
-
-
Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
-
(1993)
Chem. Phys. Lett.
, vol.208
, pp. 111
-
-
Ehlers, A.W.1
Böhme, M.2
Dapprich, S.3
Gobbi, A.4
Höllwarth, A.5
Jonas, V.6
Köhler, K.F.7
Stegmann, R.8
Veldkamp, A.9
Frenking, G.10
-
54
-
-
43949164796
-
-
Höllwarth, A.; Böhme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
-
(1993)
Chem. Phys. Lett.
, vol.208
, pp. 237
-
-
Höllwarth, A.1
Böhme, M.2
Dapprich, S.3
Ehlers, A.W.4
Gobbi, A.5
Jonas, V.6
Köhler, K.F.7
Stegmann, R.8
Veldkamp, A.9
Frenking, G.10
-
56
-
-
12344337689
-
-
Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 366
-
-
Christmann, U.1
Vilar, R.2
-
57
-
-
33847229867
-
-
For theoretical studies see: (a)
-
For theoretical studies see: (a) Lam, K. C.; Marder, T. B.; Lin, Z. Organometallics 2007, 26, 758.
-
(2007)
Organometallics
, vol.26
, pp. 758
-
-
Lam, K.C.1
Marder, T.B.2
Lin, Z.3
-
59
-
-
51049108168
-
-
(c) Li, Z.; Fu, Y.; Guo, Q.-X.; Liu, L. Organometallics 2008, 27, 4043.
-
(2008)
Organometallics
, vol.27
, pp. 4043
-
-
Li, Z.1
Fu, Y.2
Guo, Q.-X.3
Liu, L.4
-
60
-
-
0037077602
-
-
(a) Stambuli, J. P.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9346
-
-
Stambuli, J.P.1
Bühl, M.2
Hartwig, J.F.3
-
61
-
-
55049112976
-
-
(b) Moncho, S.; Ujaque, G.; Lledos, A.; Espinet, P. Chem.sEur. J. 2008, 14, 8986.
-
(2008)
Chem.sEur. J.
, vol.14
, pp. 8986
-
-
Moncho, S.1
Ujaque, G.2
Lledos, A.3
Espinet, P.4
-
62
-
-
70349625095
-
-
note
-
- is endergonic by 36.8 kcal/mol supporting the argument that the transmetalation through an open pathway is an unfeasible proposal.
-
-
-
-
63
-
-
70349617962
-
-
note
-
3)Pd-(Ar)(Br)(THF).
-
-
-
-
64
-
-
0345733884
-
-
The free energy barrier in solution should be a few kcal/mol smaller than in the gas phase because in solution the rotational and translational motions are suppressed. (a)
-
The free energy barrier in solution should be a few kcal/mol smaller than in the gas phase because in solution the rotational and translational motions are suppressed. (a) Tamura, H.; Yamasaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 16114
-
-
Tamura, H.1
Yamasaki, H.2
Sato, H.3
Sakaki, S.4
-
65
-
-
84962385341
-
-
(b) Sumimoto, M.; Iwane, N.; Takahama, T.; Sakaki, S. J. Am. Chem. Soc. 2004, 126, 10457.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 10457
-
-
Sumimoto, M.1
Iwane, N.2
Takahama, T.3
Sakaki, S.4
-
66
-
-
1642367216
-
-
(c) Sakaki, S.; Takayama, T.; Sumimoto, M.; Sugimoto, M. J. Am. Chem. Soc. 2004, 126, 3332.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3332
-
-
Sakaki, S.1
Takayama, T.2
Sumimoto, M.3
Sugimoto, M.4
-
67
-
-
84962429991
-
-
(d) Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647.
-
(2006)
Organometallics
, vol.25
, pp. 3647
-
-
Braga, A.A.C.1
Ujaque, G.2
Maseras, F.3
-
70
-
-
3743119954
-
-
We are aware of the fact that the Ph-vinyl reductive elimination occurs preferentially through four coordinate complexes when L is not a very bulky ligand (see below reference). To simplify the comparison between the energy profiles given in Figures 1-3, we have restricted our analysis solely to the reductive elimination reaction from three coordinate complexes. This choice does not affect the conclusions drawn, because the Ph-vinyl reductive elimination reaction from a Pd(II) complex is very fast
-
We are aware of the fact that the Ph-vinyl reductive elimination occurs preferentially through four coordinate complexes when L is not a very bulky ligand (see below reference). To simplify the comparison between the energy profiles given in Figures 1-3, we have restricted our analysis solely to the reductive elimination reaction from three coordinate complexes. This choice does not affect the conclusions drawn, because the Ph-vinyl reductive elimination reaction from a Pd(II) complex is very fast: Brown, J. M.; Cooley, N. A. Chem. Rev. 1988, 88, 1031.
-
(1988)
Chem. Rev.
, vol.88
, pp. 1031
-
-
Brown, J.M.1
Cooley, N.A.2
-
71
-
-
70349614917
-
-
note
-
2 occurs, the product is most likely to be four coordinated.
-
-
-
-
72
-
-
70349623429
-
-
note
-
3 substitution reaction is highly endergonic.
-
-
-
-
74
-
-
68549092330
-
-
(b) Pérez-Rodríguez, M.; Braga, A. A. C.; Garcia-Melchor, M.; Pérez-Temprano, M. H.; Casares, J. A.; Ujaque, G.; Lera, A. R.; de Alvarez, R.; Maseras, F.; Espinet, P. J. Am. Chem. Soc. 2009, 131, 3650.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3650
-
-
Pérez-Rodríguez, M.1
Braga, A.A.C.2
Garcia-Melchor, M.3
Pérez-Temprano, M.H.4
Casares, J.A.5
Ujaque, G.6
Lera, A.R.7
De Alvarez, R.8
Maseras, F.9
Espinet, P.10
-
76
-
-
34547093220
-
-
We have recently shown that the contribution of the phosphine-to-Pd σ-donation to the strength of Pd-phosphine bonding in Pd(II) complexes is much more important than of the Pd-to-phosphine π-back bonding (see below reference). It is thus reasonable to expect a positive correlation between the ó-donating ability of phosphines and the Pd-phosphine bond energies
-
We have recently shown that the contribution of the phosphine-to-Pd σ-donation to the strength of Pd-phosphine bonding in Pd(II) complexes is much more important than of the Pd-to-phosphine π-back bonding (see below reference). It is thus reasonable to expect a positive correlation between the ó-donating ability of phosphines and the Pd-phosphine bond energies: Fazaeli, R.; Ariafard, A.; Jamshidi, S.; Tabatabaie, E. S.; Pishro, K. A. J. Organomet. Chem. 2007, 692, 3984.
-
(2007)
J. Organomet. Chem.
, vol.692
, pp. 3984
-
-
Fazaeli, R.1
Ariafard, A.2
Jamshidi, S.3
Tabatabaie, E.S.4
Pishro, K.A.5
-
77
-
-
84961985327
-
-
2Pd(I)(Ph)
-
2Pd(I)(Ph): Sugiyama, A.; Ohnishi, Y.-y.; Nakaoka, M.; Nakao, Y.; Sato, H.; Sakaki, S.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 12975.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 12975
-
-
Sugiyama, A.1
Ohnishi, Y.-Y.2
Nakaoka, M.3
Nakao, Y.4
Sato, H.5
Sakaki, S.6
Nakao, Y.7
Hiyama, T.8
-
79
-
-
0000944060
-
-
(b) Evans, M. G.; Polanyi, M. J. Chem. Soc., Faraday Trans. 1936, 32, 1340.
-
(1936)
J. Chem. Soc., Faraday Trans.
, vol.32
, pp. 1340
-
-
Evans, M.G.1
Polanyi, M.2
-
80
-
-
70349631919
-
-
note
-
3.
-
-
-
|