-
1
-
-
0003397781
-
-
(Eds.: F Diederich, P. Stang), Wiley-VCH, Weinheim
-
Negishi reactions are usually catalysed by Pd complexes. We do not intend to survey such processes in this article. Recent reports can be found in ref. [7]. For general reviews on the Negishi reactions, see: a) Metal-Catalysed Cross-Coupling Reactions (Eds.: F Diederich, P. Stang), Wiley-VCH, Weinheim, 1998;
-
(1998)
Metal-catalysed Cross-coupling Reactions
-
-
-
2
-
-
20544450502
-
-
(Eds.: A. deMeijere, F. Diederich), Wiley-VCH, Weinheim
-
b) Metal-Catalysed Cross-Coupling Reactions (Eds.: A. deMeijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
-
(2004)
Metal-catalysed Cross-coupling Reactions
-
-
-
4
-
-
21244446092
-
-
For a review on metal-catalysed couplings of alkyl halides, see: A. C. Frisch, M. Beller, Angew. Chem. 2005, 117, 680-695;
-
(2005)
Angew. Chem.
, vol.117
, pp. 680-695
-
-
Frisch, A.C.1
Beller, M.2
-
6
-
-
69249123855
-
-
For a recent review on Ni-catalysed Negishi cross-coupling reactions, see: V. B. Phapale, D. J. Cárdenas, Chem. Soc. Rev. 2009, 38, 1598-1607.
-
(2009)
Chem. Soc. Rev.
, vol.38
, pp. 1598-1607
-
-
Phapale, V.B.1
Cárdenas, D.J.2
-
7
-
-
63449111326
-
-
V. B. Phapale, E. Buñuel, M. García-Iglesias, D. J. Cárdenas, Angew. Chem. 2007, 119, 8946-8951;
-
(2007)
Angew. Chem.
, vol.119
, pp. 8946-8951
-
-
Phapale, V.B.1
Buñuel, E.2
García-Iglesias, M.3
Cárdenas, D.J.4
-
8
-
-
36749022699
-
-
Angew. Chem. Int. Ed. 2007, 46, 8790-8795.
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 8790-8795
-
-
-
9
-
-
0034674791
-
-
a) A. E. Jensen, W. Dohle, E Knöchel, Tetrahedron 2000, 56, 4197-4201;
-
(2000)
Tetrahedron
, vol.56
, pp. 4197-4201
-
-
Jensen, A.E.1
Dohle, W.2
Knöchel, E.3
-
12
-
-
38349143429
-
-
d) L. Melzig, A. Gavryushin, P. Knochel, Org. Lett. 2007, 9, 5529-5532.
-
(2007)
Org. Lett.
, vol.9
, pp. 5529-5532
-
-
Melzig, L.1
Gavryushin, A.2
Knochel, P.3
-
13
-
-
67650566611
-
-
For recent reports on Pd-catalysed Negishi couplings of aryl halides and alkyl zinc halides, see: a) C. Han, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 7532-7533;
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 7532-7533
-
-
Han, C.1
Buchwald, S.L.2
-
14
-
-
67049117860
-
-
b) B. M. Coleridge, C. S. Bello, A. Leitner, Tetrahedron Lett. 2009, 50, 4475-4477;
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 4475-4477
-
-
Coleridge, B.M.1
Bello, C.S.2
Leitner, A.3
-
15
-
-
67649352716
-
-
c) T. Iwai, T. Nakai, M. Mihara M, T. Ito, T. Mizuno, T. Ohno, Synlett 2009, 1091-1094;
-
(2009)
Synlett
, pp. 1091-1094
-
-
Iwai, T.1
Nakai, T.2
Mihara M, M.3
Ito, T.4
Mizuno, T.5
Ohno, T.6
-
17
-
-
53849123985
-
-
e) Q. Liu, H. Duan, X. Luo, Y. Tang, G. Li, R. Huang, A. Lei, Adv. Synth. Catal. 2008, 350, 1349-1354;
-
(2008)
Adv. Synth. Catal.
, vol.350
, pp. 1349-1354
-
-
Liu, Q.1
Duan, H.2
Luo, X.3
Tang, Y.4
Li, G.5
Huang, R.6
Lei, A.7
-
18
-
-
35948988432
-
-
f) X. Luo, H. Zhang, H. Duan, Q. Liu, L. Zhu, T. Z. A. Lei, Org. Lett. 2007, 9, 4571-4574;
-
(2007)
Org. Lett.
, vol.9
, pp. 4571-4574
-
-
Luo, X.1
Zhang, H.2
Duan, H.3
Liu, Q.4
Zhu, L.5
Lei, T.Z.A.6
-
19
-
-
55249105544
-
-
g) G. Manolikakes, M. A. Schade, C. Muñoz-Hernandez, H. Mayr, P. Knochel, Org. Lett. 2008, 10, 2765-2768;
-
(2008)
Org. Lett.
, vol.10
, pp. 2765-2768
-
-
Manolikakes, G.1
Schade, M.A.2
Muñoz-Hernandez, C.3
Mayr, H.4
Knochel, P.5
-
20
-
-
48849093288
-
-
h) G. Zhou, P. Ting, R. Aslanian, J. J. Piwinski, Org. Lett. 2008, 10, 2517-2520;
-
(2008)
Org. Lett.
, vol.10
, pp. 2517-2520
-
-
Zhou, G.1
Ting, P.2
Aslanian, R.3
Piwinski, J.J.4
-
21
-
-
33745472389
-
-
i)C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743-4748;
-
(2006)
Chem. Eur. J.
, vol.12
, pp. 4743-4748
-
-
O'Brien, C.J.1
Kantchev, E.A.B.2
Valente, C.3
Hadei, N.4
Chass, G.A.5
Lough, A.6
Hopkinson, A.C.7
Organ, M.G.8
-
22
-
-
33745453356
-
-
j) M. G. Organ, S. Avola, I. Dubovyk, N Hadei, E. A. B. Kantchev, C. J. O'Brien, C Valente, Chem. Eur. J. 2006, 12, 4749-4755.
-
(2006)
Chem. Eur. J.
, vol.12
, pp. 4749-4755
-
-
Organ, M.G.1
Avola, S.2
Dubovyk, I.3
Hadei, N.4
Kantchev, E.A.B.5
O'Brien, C.J.6
Valente, C.7
-
26
-
-
0040164574
-
-
Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
-
(1999)
Angew. Chem. Int. Ed.
, vol.38
, pp. 3018-3020
-
-
-
28
-
-
71549122999
-
-
note
-
2] (cod = l,5-cyclooctadiene) was less convenient too. See the Supporting Information for details on the optimisation of the reaction conditions.
-
-
-
-
30
-
-
50549098750
-
-
3 and aryl ligands do not afford trifluorotoluenes, even in the presence of oxidants: G. G. Dubinina, W. W. Brennessel, J. L. Miller, D. A. Vicic, Organometallics 2008, 27, 3933-3938.
-
(2008)
Organometallics
, vol.27
, pp. 3933-3938
-
-
Dubinina, G.G.1
Brennessel, W.W.2
Miller, J.L.3
Vicic, D.A.4
-
31
-
-
71549166425
-
-
note
-
Although DFT calculations with the basis set used cannot be employed for calculation of reliable absolute energies, the calculated activation energy values are much higher than those we obtained with the same approximations in our previous studies. For that reason and for the low activation energies we have found for the alternative pathways, we may disregard these mechanisms.
-
-
-
-
33
-
-
34250189541
-
-
A. Klein, Y. H. Budnikova, O. G. Sinyashin, J. Organomet Chem. 2007, 692, 3156-3166.
-
(2007)
J. Organomet Chem.
, vol.692
, pp. 3156-3166
-
-
Klein, A.1
Budnikova, Y.H.2
Sinyashin, O.G.3
-
35
-
-
21244483940
-
-
Angew. Chem. Int. Ed. 2005, 44, 3962-3965;
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 3962-3965
-
-
-
36
-
-
12944309312
-
-
b) Stille couplings: D. A. Powell, T. Maki, G. C Fu, J. Am. Chem. Soc. 2005, 127, 510-511;
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 510-511
-
-
Powell, D.A.1
Maki, T.2
Fu, G.C.3
-
39
-
-
0032927129
-
-
a) R. Giovannini, T. Stüdemnann, A. Devasagayaraj, G. Dussin, P. Knochel, J. Org. Chem. 1999, 64, 3544-3553;
-
(1999)
J. Org. Chem.
, vol.64
, pp. 3544-3553
-
-
Giovannini, R.1
Stüdemnann, T.2
Devasagayaraj, A.3
Dussin, G.4
Knochel, P.5
-
40
-
-
0001363192
-
-
b)M. Piber, A. E. Jensen, M. Rottländer, P. Knochel, Org. Lett. 1999, 1, 1323-1326;
-
(1999)
Org. Lett.
, vol.1
, pp. 1323-1326
-
-
Piber, M.1
Jensen, A.E.2
Rottländer, M.3
Knochel, P.4
-
46
-
-
3042734823
-
-
a) T. J. Anderson, G. D. Jones, D. A. Vicie, J. Am. Chem. Soc. 2004, 126, 8100-8101
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8100-8101
-
-
Anderson, T.J.1
Jones, G.D.2
Vicie, D.A.3
-
47
-
-
19244365078
-
-
[see also Erratum: T. J. Anderson, G. D. Jones, D. A. Vicie, J. Am. Chem. Soc. 2004, 126, 11113];
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 11113
-
-
Anderson, T.J.1
Jones, G.D.2
Vicie, D.A.3
-
48
-
-
33749519198
-
-
b) G. D. Jones, J. L. Martin, C McFarland, O. R. All en, R. E. Hall, A. D. Haley, R. J. Brandon, T. Konovalova, P. J. Desrochers, P. Pulay, D. A. Vicic, J. Am. Chem. Soc. 2006, 128, 13175-13183;
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 13175-13183
-
-
Jones, G.D.1
Martin, J.L.2
McFarland, C.3
All En, O.R.4
Hall, R.E.5
Haley, A.D.6
Brandon, R.J.7
Konovalova, T.8
Desrochers, P.J.9
Pulay, P.10
Vicic, D.A.11
-
49
-
-
25144500018
-
-
c)G.D. Jones, C. McFarland, T. J. Anderson, D. A. Vicie, Chem. Commun. 2005, 4211-4213;
-
(2005)
Chem. Commun.
, pp. 4211-4213
-
-
Jones, G.D.1
McFarland, C.2
Anderson, T.J.3
Vicie, D.A.4
-
51
-
-
71549129626
-
-
note
-
0 intermediates.
-
-
-
-
52
-
-
71549140164
-
-
note
-
2 will be coordinated to THF.
-
-
-
-
53
-
-
71549123821
-
-
note
-
-1 more stable in THF), and facile isomerisation could take place according to the behaviour of different starting structures during the geometry-optimisation calculations. We have not attempted to locate transition states for these isomerisations.
-
-
-
-
54
-
-
0141704726
-
-
Gaussian, Inc., Pittsburgh P. A
-
Gaussian 03, Revision B.03, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. E. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C Gonzalez, J. A. Pople, Gaussian, Inc., Pittsburgh P. A, 2003.
-
(2003)
Gaussian 03, Revision B.03
-
-
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.E.34
Cross, J.B.35
Adamo, C.36
Jaramillo, J.37
Gomperts, R.38
Stratmann, R.E.39
Yazyev, O.40
Austin, A.J.41
Cammi, R.42
Pomelli, C.43
Ochterski, J.W.44
Ayala, P.Y.45
Morokuma, K.46
Voth, G.A.47
Salvador, P.48
Dannenberg, J.J.49
Zakrzewski, V.G.50
Dapprich, S.51
Daniels, A.D.52
Strain, M.C.53
Farkas, O.54
Malick, D.K.55
Rabuck, A.D.56
Raghavachari, K.57
Foresman, J.B.58
Ortiz, J.V.59
Cui, Q.60
Baboul, A.G.61
Clifford, S.62
Cioslowski, J.63
Stefanov, B.B.64
Liu, G.65
Liashenko, A.66
Piskorz, P.67
Komaromi, I.68
Martin, R.L.69
Fox, D.J.70
Keith, T.71
Al-Laham, M.A.72
Peng, C.Y.73
Nanayakkara, A.74
Challacombe, M.75
Gill, P.M.W.76
Johnson, B.77
Chen, W.78
Wong, M.W.79
Gonzalez, C.80
Pople, J.A.81
more..
-
55
-
-
33751157732
-
-
a)P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627;
-
(1994)
J. Phys. Chem.
, vol.98
, pp. 11623-11627
-
-
Stephens, P.J.1
Devlin, F.J.2
Chabalowski, C.F.3
Frisch, M.J.4
-
56
-
-
0030218597
-
-
b) W. Kohn, A. D. Becke, R. G. Parr, J. Phys. Chem. 1996, 100, 12974-12980;
-
(1996)
J. Phys. Chem.
, vol.100
, pp. 12974-12980
-
-
Kohn, W.1
Becke, A.D.2
Parr, R.G.3
-
62
-
-
0345491105
-
-
c) C. Lee, W Yang, R. G. Parr, 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
|