-
1
-
-
0346749657
-
-
For reviews, see: a
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For reviews, see: (a) Kunz, K.; Scholtz, U.; Ganzer, D. Synlett 2003, 15, 2428.
-
(2003)
Synlett
, vol.15
, pp. 2428
-
-
Kunz, K.1
Scholtz, U.2
Ganzer, D.3
-
2
-
-
0345708168
-
-
(b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
-
(2003)
Angew. Chem., Int. Ed
, vol.42
, pp. 5400
-
-
Ley, S.V.1
Thomas, A.W.2
-
3
-
-
33645943023
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For applications of our copper-based catalytic systems, see: a
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For applications of our copper-based catalytic systems, see: (a) Ouali, A.; Spindler, J.-F.; Cristau, H.-J.; Taillefer, M. Adv. Synth. Catal. 2006, 348, 499.
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 499
-
-
Ouali, A.1
Spindler, J.-F.2
Cristau, H.-J.3
Taillefer, M.4
-
4
-
-
17444428667
-
-
(b) Cristau, H.-J.; Ouali, A.; Spindler, J.-F.; Taillefer, M. Chem. Eur. J. 2005, 11, 2483.
-
(2005)
Chem. Eur. J
, vol.11
, pp. 2483
-
-
Cristau, H.-J.1
Ouali, A.2
Spindler, J.-F.3
Taillefer, M.4
-
5
-
-
1642528362
-
-
(c) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Org. Lett. 2004, 6, 913.
-
(2004)
Org. Lett
, vol.6
, pp. 913
-
-
Cristau, H.-J.1
Cellier, P.P.2
Spindler, J.-F.3
Taillefer, M.4
-
6
-
-
1642479421
-
-
(d) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
-
(2004)
Eur. J. Org. Chem
, pp. 695
-
-
Cristau, H.-J.1
Cellier, P.P.2
Spindler, J.-F.3
Taillefer, M.4
-
7
-
-
9244225109
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(e) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem. Eur. J. 2004, 10, 5607.
-
(2004)
Chem. Eur. J
, vol.10
, pp. 5607
-
-
Cristau, H.-J.1
Cellier, P.P.2
Spindler, J.-F.3
Taillefer, M.4
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8
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33846188227
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For patents, see: (a) Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR 0116547, 2001.
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For patents, see: (a) Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR 0116547, 2001.
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9
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33846209283
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Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR 2833947, 2003; Chem. Abstr. 2003, 139, 69290.
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(b) Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR 2833947, 2003; Chem. Abstr. 2003, 139, 69290.
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11
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33846237006
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Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR 2840303, 2003; Chem. Abstr. 2004, 140, 16744.
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(d) Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. FR 2840303, 2003; Chem. Abstr. 2004, 140, 16744.
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12
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33846222503
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WO 03/101966
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(e) Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Ouali, A. WO 03/101966, 2003.
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(2003)
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Taillefer, M.1
Cristau, H.-J.2
Cellier, P.P.3
Spindler, J.-F.4
Ouali, A.5
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14
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33846250932
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WO 2005023731
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(g) Spindler, J.-F.; Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Ouali, A. WO 2005023731, 2005.
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(2005)
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Spindler, J.-F.1
Taillefer, M.2
Cristau, H.-J.3
Cellier, P.P.4
Ouali, A.5
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15
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33745908283
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Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J.-F. Chem. Eur. J. 2006, 12, 5301.
-
(2006)
Chem. Eur. J
, vol.12
, pp. 5301
-
-
Taillefer, M.1
Ouali, A.2
Renard, B.3
Spindler, J.-F.4
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16
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33846185212
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The four main mechanisms proposed in the literature involve (1) oxidative addition/reductive elimination of ArX on copper(I), (2) π-complexation of ArX on copper(I), (3) Lewis-type complexation of ArX on copper(I), or (4) aryl radical intermediates. None of these mechanisms have been confirmed by experimental proofs.
-
The four main mechanisms proposed in the literature involve (1) oxidative addition/reductive elimination of ArX on copper(I), (2) π-complexation of ArX on copper(I), (3) Lewis-type complexation of ArX on copper(I), or (4) aryl radical intermediates. None of these mechanisms have been confirmed by experimental proofs.
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17
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85086811067
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(a) Yumada, K.; Kubo, T.; Fukuyama, T. Synlett 2002, 2, 231.
-
(2002)
Synlett
, vol.2
, pp. 231
-
-
Yumada, K.1
Kubo, T.2
Fukuyama, T.3
-
20
-
-
0032501446
-
-
(d) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
-
(1998)
J. Am. Chem. Soc
, vol.120
, pp. 12459
-
-
Ma, D.1
Zhang, Y.2
Yao, J.3
Wu, S.4
Tao, F.5
-
21
-
-
0000139143
-
-
(e) Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
-
(1997)
J. Org. Chem
, vol.62
, pp. 2312
-
-
Zhang, S.1
Zhang, D.2
Liebeskind, L.S.3
-
22
-
-
33751386131
-
-
(f) Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
-
(1993)
J. Org. Chem
, vol.58
, pp. 4716
-
-
Okuro, K.1
Furuune, M.2
Enna, M.3
Miura, M.4
Nomura, M.5
-
23
-
-
0001199033
-
-
and references cited therein
-
(g) Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496 and references cited therein.
-
(1987)
J. Am. Chem. Soc
, vol.109
, pp. 1496
-
-
Paine, A.J.1
-
25
-
-
0345329013
-
-
and references cited therein
-
(i) Lindley, J. Tetrahedron 1984, 40, 1433 and references cited therein.
-
(1984)
Tetrahedron
, vol.40
, pp. 1433
-
-
Lindley, J.1
-
26
-
-
0001443787
-
-
(j) Bowman, W. R.; Heaney, H.; Smith, P. H. G. Tetrahedron Lett. 1984, 25, 5821.
-
(1984)
Tetrahedron Lett
, vol.25
, pp. 5821
-
-
Bowman, W.R.1
Heaney, H.2
Smith, P.H.G.3
-
29
-
-
0002845031
-
-
Cohen, T.; Wood, J.; Dietz, A. G., Jr. Tetrahedron Lett. 1974, 1, 3555.
-
(1974)
Tetrahedron Lett
, vol.1
, pp. 3555
-
-
Cohen, T.1
Wood, J.2
Dietz Jr., A.G.3
-
30
-
-
37049127778
-
-
(m) Burdon, J.; Coe, P. L.; Marsh, C. R.; Tatlow, J. J. J. Chem. Soc., Perkin Trans. 1 1972, 763.
-
(1972)
J. Chem. Soc., Perkin Trans. 1
, pp. 763
-
-
Burdon, J.1
Coe, P.L.2
Marsh, C.R.3
Tatlow, J.J.4
-
31
-
-
33846226737
-
-
(n) Sato, M.; Motoyama, I.; Hata, K. Bull. Chem. Soc. Jpn. 1970, 43, 2972.
-
(1970)
Bull. Chem. Soc. Jpn
, vol.43
, pp. 2972
-
-
Sato, M.1
Motoyama, I.2
Hata, K.3
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38
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16244411305
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However, it is worth noting that, recently, Buchwald's works suggested that the role of (dimethylamino)cyclohexane in copper-mediated arylation of amides was to avoid formation of copper complexes containing two amidates, which are unable to promote the coupling. Note that this study only concerned the particular case of amidation reactions: Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
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However, it is worth noting that, recently, Buchwald's works suggested that the role of (dimethylamino)cyclohexane in copper-mediated arylation of amides was to avoid formation of copper complexes containing two amidates, which are unable to promote the coupling. Note that this study only concerned the particular case of amidation reactions: Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120.
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39
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0000872002
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-
Colton, R.; James, B. D.; Potter, I. D.; Traeger, J. C. Inorg. Chem. 1993, 32, 2626.
-
(1993)
Inorg. Chem
, vol.32
, pp. 2626
-
-
Colton, R.1
James, B.D.2
Potter, I.D.3
Traeger, J.C.4
-
40
-
-
0000759740
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-
van Stein, G. C.; van Koten, G.; Vrieze, K.; Brevard, C.; Spek, A. L. J. Am. Chem. Soc. 1984, 106, 4486.
-
(1984)
J. Am. Chem. Soc
, vol.106
, pp. 4486
-
-
van Stein, G.C.1
van Koten, G.2
Vrieze, K.3
Brevard, C.4
Spek, A.L.5
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41
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33846239702
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3-CN (see Figure 3a): at that temperature, the coupling was slower, phenyl 3,5-dimethylphenyl ether being obtained in 26% yield after 70 h (Table 1, entry 5). Better yields can be achieved by increasing the reaction time.
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3-CN (see Figure 3a): at that temperature, the coupling was slower, phenyl 3,5-dimethylphenyl ether being obtained in 26% yield after 70 h (Table 1, entry 5). Better yields can be achieved by increasing the reaction time.
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42
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33846220807
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It was, of course, the same for all of the other protons of the complexed ligand
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It was, of course, the same for all of the other protons of the complexed ligand.
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44
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33846201780
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Brooker, S.; Davidson, T. C.; Hay, S. J.; Kelly, R. J.; Kennepohl, D. K.; Plieger, P. G.; Moubakari, B.; Murray, K. S.; Bill, E.; Bothe, E. Coord. Chem. Rev. 2001, 216-217, 3. This study deals with a tetracopper(I) complex involving the octadentate ligand L. L. comprising four imine nitrogen donors and four pyridazine nitrogen donors, could thus be regarded as a dimer of our tetradentate ligand 1. According to proton NMR spectra, the structure of the tetracopper(I) complex was maintained in noncoordinating solvents such as nitromethane and acetone, whereas in acetonitrile, the latter existed in equilibrium with a dicopper(I) complex, resulting from the opening of the tetramer under the effect of the solvent.
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Brooker, S.; Davidson, T. C.; Hay, S. J.; Kelly, R. J.; Kennepohl, D. K.; Plieger, P. G.; Moubakari, B.; Murray, K. S.; Bill, E.; Bothe, E. Coord. Chem. Rev. 2001, 216-217, 3. This study deals with a tetracopper(I) complex involving the octadentate ligand L. L. comprising four imine nitrogen donors and four pyridazine nitrogen donors, could thus be regarded as a "dimer" of our tetradentate ligand 1. According to proton NMR spectra, the structure of the tetracopper(I) complex was maintained in noncoordinating solvents such as nitromethane and acetone, whereas in acetonitrile, the latter existed in equilibrium with a dicopper(I) complex, resulting from the opening of the tetramer under the effect of the solvent.
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45
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0000862310
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1st ed, Wilkinson, G, Gaillard, R. D, McCleverty J. A, Eds, Pergamon Press: Oxford, U.K
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Hathaway, B. J. In Comprehensive Coordination Chemistry, 1st ed.; Wilkinson, G., Gaillard, R. D., McCleverty J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. 5, pp 536-537.
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(1987)
Comprehensive Coordination Chemistry
, vol.5
, pp. 536-537
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Hathaway, B.J.1
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47
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33846200903
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The solubility of this complex is also very weak, even on reflux in acetonitrile
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The solubility of this complex is also very weak, even on reflux in acetonitrile.
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48
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0030700314
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Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
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(1997)
J. Am. Chem. Soc
, vol.119
, pp. 10539
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Marcoux, J.F.1
Doye, S.2
Buchwald, S.L.3
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49
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33846194718
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Not only at 80°C but also at 40°C (monomer exclusively present, Figure 3a), the 2b-catalyzed copper arylation of 3,5-dimethylphenol with iodobenzene takes place (no reaction without ligand at 40°C) (Table 1). The yield after 24 h is, however, relatively average (26%, Table 1, entry 5), thus accounting for the low reaction temperature.
-
Not only at 80°C but also at 40°C (monomer exclusively present, Figure 3a), the 2b-catalyzed copper arylation of 3,5-dimethylphenol with iodobenzene takes place (no reaction without ligand at 40°C) (Table 1). The yield after 24 h is, however, relatively average (26%, Table 1, entry 5), thus accounting for the low reaction temperature.
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52
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33845379142
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Dieter, R. K.; Silks, L. A.. III; Fishpaugh, J. R.; Kastner, M. E. J. Am. Chem. Soc. 1985, 107, 4679.
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Dieter, R. K.; Silks, L. A.. III; Fishpaugh, J. R.; Kastner, M. E. J. Am. Chem. Soc. 1985, 107, 4679.
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54
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33846186061
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The coexistence of monomer and dimer in the solution led to a high complexity of the signals for cyclohexane protons, thus preventing us from assigning precisely this part of the spectrum
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The coexistence of monomer and dimer in the solution led to a high complexity of the signals for cyclohexane protons, thus preventing us from assigning precisely this part of the spectrum.
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