-
3
-
-
46649098072
-
-
Michelet, V.; Toullec, P. Y.; Genet, J. P. Angew. Chem., Int. Ed. 2008, 47, 4268-4315
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 4268-4315
-
-
Michelet, V.1
Toullec, P.Y.2
Genet, J.P.3
-
7
-
-
34250824768
-
-
Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410-3449
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 3410-3449
-
-
Fürstner, A.1
Davies, P.W.2
-
9
-
-
29544447401
-
-
Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200-203
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 200-203
-
-
Ma, S.1
Yu, S.2
Gu, Z.3
-
11
-
-
38349014690
-
-
Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718-721
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 718-721
-
-
Correa, A.1
Marion, N.2
Fensterbank, L.3
Malacria, M.4
Nolan, S.P.5
Cavallo, L.6
-
12
-
-
39749109929
-
-
Aponick, A.; Li, C.; Berenger, B. Org. Lett. 2008, 10, 669-671
-
(2008)
Org. Lett.
, vol.10
, pp. 669-671
-
-
Aponick, A.1
Li, C.2
Berenger, B.3
-
13
-
-
34547556193
-
-
Marion, N.; Carlqvist, P.; Gealageas, R.; de Frémont, P.; Maseras, F.; Nolan, S. P. Chem. - Eur. J. 2007, 13, 6437-6451
-
(2007)
Chem. - Eur. J.
, vol.13
, pp. 6437-6451
-
-
Marion, N.1
Carlqvist, P.2
Gealageas, R.3
De Frémont, P.4
Maseras, F.5
Nolan, S.P.6
-
14
-
-
23044485049
-
-
Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500-10501
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 10500-10501
-
-
Sromek, A.W.1
Rubina, M.2
Gevorgyan, V.3
-
15
-
-
79952638288
-
-
Nijamudheen, A.; Jose, D.; Datta, A. J. Phys. Chem. C 2011, 115, 2187-2195
-
(2011)
J. Phys. Chem. C
, vol.115
, pp. 2187-2195
-
-
Nijamudheen, A.1
Jose, D.2
Datta, A.3
-
16
-
-
52049117956
-
-
Cordonnier, M. C.; Blanc, A.; Pale, P. Org. Lett. 2008, 10, 1569-1572
-
(2008)
Org. Lett.
, vol.10
, pp. 1569-1572
-
-
Cordonnier, M.C.1
Blanc, A.2
Pale, P.3
-
17
-
-
65249145686
-
-
González-Pérez, A.; Silva, C.; Marco-Contelles, J. L.; Faza, O. N.; Soriano, E.; de Lera, A. R. J. Org. Chem. 2009, 74, 2982-2991
-
(2009)
J. Org. Chem.
, vol.74
, pp. 2982-2991
-
-
González-Pérez, A.1
Silva, C.2
Marco-Contelles, J.L.3
Faza, O.N.4
Soriano, E.5
De Lera, A.R.6
-
18
-
-
33845376099
-
-
Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1996, 108, 6405-6406
-
(1996)
J. Am. Chem. Soc.
, vol.108
, pp. 6405-6406
-
-
Ito, Y.1
Sawamura, M.2
Hayashi, T.3
-
19
-
-
53249151254
-
-
Bongers, N.; Krause, N. Angew. Chem., Int. Ed. 2008, 47, 2178-2181
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 2178-2181
-
-
Bongers, N.1
Krause, N.2
-
20
-
-
33846047998
-
-
Zhang, Z.; Widenhoefer, R. A. Angew. Chem., Int. Ed. 2007, 46, 283-285
-
(2007)
Angew. Chem., Int. Ed.
, vol.46
, pp. 283-285
-
-
Zhang, Z.1
Widenhoefer, R.A.2
-
21
-
-
15944427478
-
-
Muñoz, M. P.; Adrio, J.; Carretero, J. C.; Echavarren, A. M. Organometallics 2005, 24, 1293-1300
-
(2005)
Organometallics
, vol.24
, pp. 1293-1300
-
-
Muñoz, M.P.1
Adrio, J.2
Carretero, J.C.3
Echavarren, A.M.4
-
22
-
-
23044449420
-
-
González-Arellano, C.; Corma, A.; Iglesias, M.; Sánchez, F. Chem. Commun. 2005, 3451-3453
-
(2005)
Chem. Commun.
, pp. 3451-3453
-
-
González-Arellano, C.1
Corma, A.2
Iglesias, M.3
Sánchez, F.4
-
23
-
-
34547567515
-
-
Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, D. Science 2007, 317, 496-499
-
(2007)
Science
, vol.317
, pp. 496-499
-
-
Hamilton, G.L.1
Kang, E.J.2
Mba, M.3
Toste, D.4
-
27
-
-
33745677660
-
-
Sherry, B. D.; Maus, L.; Laforteza, B. N.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 8132-8133
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 8132-8133
-
-
Sherry, B.D.1
Maus, L.2
Laforteza, B.N.3
Toste, F.D.4
-
28
-
-
52049110849
-
-
Shu, X.; Liu, X.; Ji, K.; Xiao, H.; Liang, Y. Chem. - Eur. J. 2008, 14, 5282-5290
-
(2008)
Chem. - Eur. J.
, vol.14
, pp. 5282-5290
-
-
Shu, X.1
Liu, X.2
Ji, K.3
Xiao, H.4
Liang, Y.5
-
29
-
-
17744400103
-
-
Shi, X.; Gorin, D. J.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 5802-5803
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 5802-5803
-
-
Shi, X.1
Gorin, D.J.2
Toste, F.D.3
-
31
-
-
33644555190
-
-
Faza, O. N.; Silva, C.; Álvarez, R.; de Lera, A. R. J. Am. Chem. Soc. 2006, 128, 2434-2437
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 2434-2437
-
-
Faza, O.N.1
Silva, C.2
Álvarez, R.3
De Lera, A.R.4
-
32
-
-
66349094524
-
-
Zhang, J.; Shen, W.; Li, L.; Li, M. Organometallics 2009, 28, 3129-3139
-
(2009)
Organometallics
, vol.28
, pp. 3129-3139
-
-
Zhang, J.1
Shen, W.2
Li, L.3
Li, M.4
-
33
-
-
77953116518
-
-
Dudnik, A. S.; Xia, Y.; Li, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 7645-7655
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 7645-7655
-
-
Dudnik, A.S.1
Xia, Y.2
Li, Y.3
Gevorgyan, V.4
-
34
-
-
79956127825
-
-
Another possible evolution of the system after 8 would be nucleophilic attack of a free alkoxide on a gold-activated alkyne, to yield structures analogous to 4 or 5. Analysis of all the transition states characterized for such a step seem to point to the previous formation of a C-O bond on the aromatic ring. One of them is only slightly lower in energy than ts87 (53.51 kcal/mol with respect to 2, vs 56.07 kcal/mol); the other is significantly more energetic (72.79 kcal/mol), further supporting the inviability of this path
-
Another possible evolution of the system after 8 would be nucleophilic attack of a free alkoxide on a gold-activated alkyne, to yield structures analogous to 4 or 5. Analysis of all the transition states characterized for such a step seem to point to the previous formation of a C-O bond on the aromatic ring. One of them is only slightly lower in energy than ts87 (53.51 kcal/mol with respect to 2, vs 56.07 kcal/mol); the other is significantly more energetic (72.79 kcal/mol), further supporting the inviability of this path.
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-
-
-
35
-
-
79956097487
-
-
The analogous syn transition structure is 7.41 kcal/mol more energetic than ts23a
-
The analogous syn transition structure is 7.41 kcal/mol more energetic than ts23a.
-
-
-
-
36
-
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79956110291
-
-
See Supporting Information for tables with the most relevant geometric parameters
-
See Supporting Information for tables with the most relevant geometric parameters.
-
-
-
-
37
-
-
79956136746
-
-
note
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7 distance for the latter, even if their electronic energies are surprisingly close. After ts45, though, the chosen reaction coordinate seems to accurately describe the transformations taking place, and the structure and relative energy of ts56a closely correspond to a point in the curve.
-
-
-
-
38
-
-
60749094741
-
-
Faza, O. N.; Silva, C.; Álvarez, R.; de Lera, A. R. Chem. - Eur. J. 2009, 15, 1944-1956
-
(2009)
Chem. - Eur. J.
, vol.15
, pp. 1944-1956
-
-
Faza, O.N.1
Silva, C.2
Álvarez, R.3
De Lera, A.R.4
-
39
-
-
4644249343
-
-
Faza, O. N.; Silva, C.; Álvarez, R.; de Lera, A. R. Chem. - Eur. J. 2004, 10, 4324-4333
-
(2004)
Chem. - Eur. J.
, vol.10
, pp. 4324-4333
-
-
Faza, O.N.1
Silva, C.2
Álvarez, R.3
De Lera, A.R.4
-
40
-
-
25144477786
-
-
Faza, O. N.; Silva, C.; Álvarez, R.; de Lera, A. R. Chem. Commun. 2005, 4285-4287
-
(2005)
Chem. Commun.
, pp. 4285-4287
-
-
Faza, O.N.1
Silva, C.2
Álvarez, R.3
De Lera, A.R.4
-
41
-
-
0011190497
-
-
Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; v. Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317-6318
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 6317-6318
-
-
Schleyer V. P, R.1
Maerker, C.2
Dransfeld, A.3
Jiao, H.4
Eikema Hommes, N.J.R.V.5
-
42
-
-
27744463786
-
-
Geuenich, D.; Hess, K.; Köhler, F.; Herges, R. Chem. Rev. 2005, 105, 3758-3772
-
(2005)
Chem. Rev.
, vol.105
, pp. 3758-3772
-
-
Geuenich, D.1
Hess, K.2
Köhler, F.3
Herges, R.4
-
43
-
-
79956098811
-
-
note
-
Along the reaction coordinate of a pentadienyl cation cyclization, there is a displacement of the positive charge from odd to even positions, so a donor on an even position will at the same time stabilize the transition state and the product and destabilize the reactant, resulting in a lower barrier for the reaction. Such a substitution also contributes to a larger polarization of the cycling chain, which also helps lower the activation energy.
-
-
-
-
45
-
-
15744375697
-
-
Gaussian, Inc., Wallingford, CT
-
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc., Wallingford, CT, 2004.
-
(2004)
Gaussian 03, Revision C.02
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Bakken, V.36
Adamo, C.37
Jaramillo, J.38
Gomperts, R.39
Stratmann, R.E.40
Yazyev, O.41
Austin, A.J.42
Cammi, R.43
Pomelli, C.44
Ochterski, J.W.45
Ayala, P.Y.46
Morokuma, K.47
Voth, G.A.48
Salvador, P.49
Dannenberg, J.J.50
Zakrzewski, V.G.51
Dapprich, S.52
Daniels, A.D.53
Strain, M.C.54
Farkas, O.55
Malick, D.K.56
Rabuck, A.D.57
Raghavachari, K.58
Foresman, J.B.59
Ortiz, J.V.60
Cui, Q.61
Baboul, A.G.62
Clifford, S.63
Cioslowski, J.64
Stefanov, B.B.65
Liu, G.66
Liashenko, A.67
Piskorz, P.68
Komaromi, I.69
Martin, R.L.70
Fox, D.J.71
Keith, T.72
Al-Laham, M.A.73
Peng, C.Y.74
Nanayakkara, A.75
Challacombe, M.76
Gill, P.M.W.77
Johnson, B.78
Chen, W.79
Wong, M.W.80
Gonzalez, C.81
Pople, J.A.82
more..
-
46
-
-
79956114963
-
-
Orca 2.7.0
-
Neese, F. Orca 2.7.0. http://www.thch.uni-bonn.de/tc/orca/.
-
-
-
Neese, F.1
-
50
-
-
0345491105
-
-
Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785-789
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
51
-
-
11744322674
-
-
Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-141
-
(1990)
Theor. Chim. Acta
, vol.77
, pp. 123-141
-
-
Andrae, D.1
Häussermann, U.2
Dolg, M.3
Stoll, H.4
Preuss, H.5
-
54
-
-
79952185516
-
-
Faza, O. N.; Álvarez-Rodríguez, R.; Silva-López, C. Theor. Chem. Acc. 2011, 128, 647-661
-
(2011)
Theor. Chem. Acc.
, vol.128
, pp. 647-661
-
-
Faza, O.N.1
Álvarez-Rodríguez, R.2
Silva-López, C.3
-
56
-
-
26344435738
-
-
Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
-
(1992)
J. Chem. Phys.
, vol.97
, pp. 2571-2577
-
-
Schaefer, A.1
Horn, H.2
Ahlrichs, R.3
-
58
-
-
0039128076
-
-
Schwerdtfeger, P.; Dolg, M.; Schwarz, W. H. E.; Bowmaker, G. A.; Boyd, P. D. W. J. Chem. Phys. 1989, 91, 1762-1774
-
(1989)
J. Chem. Phys.
, vol.91
, pp. 1762-1774
-
-
Schwerdtfeger, P.1
Dolg, M.2
Schwarz, W.H.E.3
Bowmaker, G.A.4
Boyd, P.D.W.5
-
60
-
-
79956134299
-
-
2 as solvent. However, gas-phase energy values have been used in all our discussions, because of the large errors introduced in the calculation of solvation energies in charged systems. The calculated solvation energies (see Supporting Information) span, nevertheless, a limited range of 2.74 kcal/mol that would not alter any of the conclusions of the study
-
2 as solvent. However, gas-phase energy values have been used in all our discussions, because of the large errors introduced in the calculation of solvation energies in charged systems. The calculated solvation energies (see Supporting Information) span, nevertheless, a limited range of 2.74 kcal/mol that would not alter any of the conclusions of the study.
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