-
1
-
-
78349276726
-
-
Recent reviews on copper-catalyzed Ullmann-type coupling reaction, see
-
Recent reviews on copper-catalyzed Ullmann-type coupling reaction, see
-
-
-
-
3
-
-
70349786460
-
-
Angew. Chem. Int. Ed. 2009, 48, 6954 - 6971
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 6954-6971
-
-
-
4
-
-
51049095122
-
-
G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054 - 3131
-
(2008)
Chem. Rev.
, vol.108
, pp. 3054-3131
-
-
Evano, G.1
Blanchard, N.2
Toumi, M.3
-
6
-
-
41149131770
-
-
M. Carril, R. SanMartin, E. Domínguez, Chem. Soc. Rev. 2008, 37, 639 - 647
-
(2008)
Chem. Soc. Rev.
, vol.37
, pp. 639-647
-
-
Carril, M.1
Sanmartin, R.2
Domínguez, E.3
-
7
-
-
34548296982
-
-
4176, and references cited therein.
-
M. Kienle, S. R. Dubbaka, K. Brade, P. Knochel, Eur. J. Org. Chem. 2007, 4166 - 4176, and references cited therein.
-
(2007)
Eur. J. Org. Chem.
, pp. 4166
-
-
Kienle, M.1
Dubbaka, S.R.2
Brade, K.3
Knochel, P.4
-
10
-
-
0034794463
-
-
A. Klapars, J. C. Antilla, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7727 - 7729.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 7727-7729
-
-
Klapars, A.1
Antilla, J.C.2
Huang, X.3
Buchwald, S.L.4
-
11
-
-
0032501446
-
-
D. Ma, Y. Zhang, J. Yao, S. Wu, T. Tao, J. Am. Chem. Soc. 1998, 120, 12459 - 12467.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 12459-12467
-
-
Ma, D.1
Zhang, Y.2
Yao, J.3
Wu, S.4
Tao, T.5
-
12
-
-
78349258337
-
-
French Patents 16547, Fr 2833947-WO0353225.
-
M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, French Patents 16547, Fr 2833947-WO0353225, 2001.
-
(2001)
-
-
Taillefer, M.1
Cristau, H.-J.2
Cellier, P.P.3
Spindler, J.-F.4
-
15
-
-
33847207721
-
-
K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292
-
(2006)
Angew. Chem.
, vol.118
, pp. 7292
-
-
Nicolaou, K.C.1
Edmonds, D.J.2
Bulger, P.G.3
-
16
-
-
33750977591
-
-
Angew. Chem. Int. Ed. 2006, 45, 7134 -7186
-
(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 7134-7186
-
-
-
17
-
-
20444486970
-
-
A. de Meijere, P. von Zezschwitz, S. Bräse, Acc. Chem. Res. 2005, 38, 413 - 422
-
(2005)
Acc. Chem. Res.
, vol.38
, pp. 413-422
-
-
De Meijere, A.1
Von Zezschwitz, P.2
Bräse, S.3
-
18
-
-
2942557280
-
-
2198 and references cited therein.
-
I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127 - 2198 and references cited therein.
-
(2004)
Chem. Rev.
, vol.104
, pp. 2127
-
-
Nakamura, I.1
Yamamoto, Y.2
-
19
-
-
17444401687
-
-
J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001 - 1020.
-
(2005)
Chem. Rev.
, vol.105
, pp. 1001-1020
-
-
Wasilke, J.-C.1
Obrey, S.J.2
Baker, R.T.3
Bazan, G.C.4
-
20
-
-
78349254021
-
-
Limited examples have appeared for the low catalyst loading copper-mediated reaction. Taillefer et al. showed that only 10 ppm of Cu was enough for the coupling at 80°C of PhI and phenols, see
-
Limited examples have appeared for the low catalyst loading copper-mediated reaction. Taillefer et al. showed that only 10 ppm of Cu was enough for the coupling at 80°C of PhI and phenols, see
-
-
-
-
21
-
-
78349274194
-
-
505, and references cited therein. Bolm recently reported the C-N bond coupling reaction using a part-per-million catalyst loading with an excess (20 mol%) of ligand, see
-
A. Ouali, J.-F. Spindler, H.-J. Cristau, M. Taillefer, Adv. Synth. Catal. 2006, 348, 449 - 505, and references cited therein. Bolm recently reported the C-N bond coupling reaction using a part-per-million catalyst loading with an excess (20 mol%) of ligand, see
-
(2006)
Adv. Synth. Catal.
, vol.348
, pp. 449
-
-
Ouali, A.1
Spindler, J.-F.2
Cristau, H.-J.3
Taillefer, M.4
-
22
-
-
71949123493
-
-
P.-F. Larsson, A. Correa, M. Carril, P.-O. Norrby, C. Bolm, Angew. Chem. 2009, 121, 5801 - 5803
-
(2009)
Angew. Chem.
, vol.121
, pp. 5801-5803
-
-
Larsson, P.-F.1
Correa, A.2
Carril, M.3
Norrby, P.-O.4
Bolm, C.5
-
23
-
-
70349929617
-
-
Angew. Chem. Int. Ed. 2009, 48, 5691 - 5693.
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 5691-5693
-
-
-
24
-
-
72049108891
-
-
O. O. Ajani, C. A. Obafemi, O. C. Nwinyi, D. A. Akinpelu, Bioorg. Med. Chem. 2010, 18, 214 - 221
-
(2010)
Bioorg. Med. Chem.
, vol.18
, pp. 214-221
-
-
Ajani, O.O.1
Obafemi, C.A.2
Nwinyi, O.C.3
Akinpelu, D.A.4
-
25
-
-
62949241322
-
-
X. Bailing, B. Xu, Y. Sun, Y. Guo, Y. Cao, T. Yu, Bioorg. Med. Chem. 2009, 17, 2767 - 2774
-
(2009)
Bioorg. Med. Chem.
, vol.17
, pp. 2767-2774
-
-
Bailing, X.1
Xu, B.2
Sun, Y.3
Guo, Y.4
Cao, Y.5
Yu, T.6
-
26
-
-
58549085379
-
-
D. V. Smil, S. Manku, Y. A. Chantigny, S. Leit, A. Wahhab, T. P. Yan, M. Fournel, C. Maroun, Z. Li, A.-M. Lemieux, A. Nicolescu, J. Rahil, S. Lefebvre, A. Panetta, J. M. Besterman, R. Déziel., Bioorg. Med. Chem. Lett., 2009, 19, 688 - 692
-
(2009)
Bioorg. Med. Chem. Lett.
, vol.19
, pp. 688-692
-
-
Smil, D.V.1
Manku, S.2
Chantigny, Y.A.3
Leit, S.4
Wahhab, A.5
Yan, T.P.6
Fournel, M.7
Maroun, C.8
Li, Z.9
Lemieux, A.-M.10
Nicolescu, A.11
Rahil, J.12
Lefebvre, S.13
Panetta, A.14
Besterman, J.M.15
Déziel, R.16
-
27
-
-
43449108293
-
-
Y. Mori, T. Hirokawa, K. Aoki, H. Satomi, S. Takeda, M. Aburada, K. Miyamoto, Chem. Pharm. Bull. 2008, 56, 682 - 687
-
(2008)
Chem. Pharm. Bull.
, vol.56
, pp. 682-687
-
-
Mori, Y.1
Hirokawa, T.2
Aoki, K.3
Satomi, H.4
Takeda, S.5
Aburada, M.6
Miyamoto, K.7
-
28
-
-
0038004032
-
-
2302, and references cited therein.
-
U. J. Ries, H. W. M. Priepke, N. H. Hauel, S. Handschuh, G. Mihm, J. M. Stassen, W. Wienen, H. Nar., Bioorg. Med. Chem. Lett., 2003, 13, 2297 - 2302, and references cited therein.
-
(2003)
Bioorg. Med. Chem. Lett.
, vol.13
, pp. 2297
-
-
Ries, U.J.1
Priepke, H.W.M.2
Hauel, N.H.3
Handschuh, S.4
Mihm, G.5
Stassen, J.M.6
Wienen, W.7
-
29
-
-
85010154107
-
-
G. Sakata, T. Inukai, H. Hirata, K. Suzuki, J. Pestic. Sci. 1991, 16, 315 - 323.
-
(1991)
J. Pestic. Sci.
, vol.16
, pp. 315-323
-
-
Sakata, G.1
Inukai, T.2
Hirata, H.3
Suzuki, K.4
-
30
-
-
67649983992
-
-
J. Miyashiro, K. W. Woods, C. H. Park, X. Liu, Y. Shi, E. F. Johnson, J. J. Bouska, A. M. Olson, Y. Luo, E. H. Fry, V. L. Giranda, T. D. Penning, Bioorg. Med. Chem. Lett. 2009, 19, 4050 - 4054.
-
(2009)
Bioorg. Med. Chem. Lett.
, vol.19
, pp. 4050-4054
-
-
Miyashiro, J.1
Woods, K.W.2
Park, C.H.3
Liu, X.4
Shi, Y.5
Johnson, E.F.6
Bouska, J.J.7
Olson, A.M.8
Luo, Y.9
Fry, E.H.10
Giranda, V.L.11
Penning, T.D.12
-
31
-
-
67649975255
-
-
J.-L. Li, B. Han, K. Jiang, W. Du, Y.-C. Chen, Bioorg. Med. Chem. Lett. 2009, 19, 3952 - 3954.
-
(2009)
Bioorg. Med. Chem. Lett.
, vol.19
, pp. 3952-3954
-
-
Li, J.-L.1
Han, B.2
Jiang, K.3
Du, W.4
Chen, Y.-C.5
-
32
-
-
57549091820
-
-
A. Alizadeh, M. Babaki, N. Zohreh, A. Rezvanian, Synthesis 2008, 3793 - 3796.
-
(2008)
Synthesis
, pp. 3793-3796
-
-
Alizadeh, A.1
Babaki, M.2
Zohreh, N.3
Rezvanian, A.4
-
33
-
-
67649993442
-
-
S. Tanimori, T. Nishimura, M. Kirihata, Bioorg. Med. Chem. Lett. 2009, 19, 4119 - 4121.
-
(2009)
Bioorg. Med. Chem. Lett.
, vol.19
, pp. 4119-4121
-
-
Tanimori, S.1
Nishimura, T.2
Kirihata, M.3
-
34
-
-
78349288251
-
-
See Supporting Information.
-
See Supporting Information.
-
-
-
-
35
-
-
78349250733
-
-
When 1.0 and 1.5 equiv. of L -phenylalanine were employed, the yields were decreased to 17% and 50%, respectively, under the optimized conditions.
-
When 1.0 and 1.5 equiv. of L -phenylalanine were employed, the yields were decreased to 17% and 50%, respectively, under the optimized conditions.
-
-
-
-
36
-
-
78349237116
-
-
It is assumed that the nitrogen-oxygen interchange through the rubber of the balloon could occur to prevent the catalytic activity.
-
It is assumed that the nitrogen-oxygen interchange through the rubber of the balloon could occur to prevent the catalytic activity.
-
-
-
-
37
-
-
78349231456
-
-
Although it is easy to remove the inorganic base from the reaction mixture by aqueous work-up, a large amount of aqueous waste containing inorganic salts is produced and it is costly for disposal. Another advantage with the use of DBU was the ease of the purification process, which avoided the elaboration of unsoluble materials frequently observed when inorganic salts were employed as base to prevent the easy isolation of product.
-
Although it is easy to remove the inorganic base from the reaction mixture by aqueous work-up, a large amount of aqueous waste containing inorganic salts is produced and it is costly for disposal. Another advantage with the use of DBU was the ease of the purification process, which avoided the elaboration of unsoluble materials frequently observed when inorganic salts were employed as base to prevent the easy isolation of product.
-
-
-
-
39
-
-
62949241322
-
-
2774, and references cited therein.
-
B. Xu, Y. Sun. Y. Guo, Y. Gao, T. Yu, Bioorg. Med. Chem. 2009, 17, 2767 - 2774, and references cited therein.
-
(2009)
Bioorg. Med. Chem.
, vol.17
, pp. 2767
-
-
Xu, B.1
Guo, Y.Sun.Y.2
Gao, Y.3
Yu, T.4
-
40
-
-
78349279770
-
-
Recent reports dealing with the chiral synthesis of 3-substituted qionoxalin-2-ones, see
-
Recent reports dealing with the chiral synthesis of 3-substituted qionoxalin-2-ones, see
-
-
-
-
42
-
-
33750071714
-
-
C. Y. Abraham, D. H. Paull, M. T. Scerba, J. W. Grebinski, T. Lectka, J. Am. Chem. Soc. 2006, 128, 12370 - 12371
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 12370-12371
-
-
Abraham, C.Y.1
Paull, D.H.2
Scerba, M.T.3
Grebinski, J.W.4
Lectka, T.5
-
43
-
-
34547621822
-
-
Q. Jiang, D. Jiang, Y. Jiang, H. Fu, Y. Zhao, Synlett 2007, 1836 - 1842
-
(2007)
Synlett
, pp. 1836-1842
-
-
Jiang, Q.1
Jiang, D.2
Jiang, Y.3
Fu, H.4
Zhao, Y.5
-
44
-
-
77149176225
-
-
M. Rueping, F. Tato, F. R. Schoepke, Chem. Eur. J. 2010, 16, 2688 - 2691.
-
(2010)
Chem. Eur. J.
, vol.16
, pp. 2688-2691
-
-
Rueping, M.1
Tato, F.2
Schoepke, F.R.3
-
45
-
-
0035230425
-
-
K. H. P. Moore, L. M. Cass, N. Dallow, T. C. Hardman, A. Jones, M. Boyce, W. T. Prince, Eur. J. Clin. Pharmacol. 2001, 56, 805 - 811.
-
(2001)
Eur. J. Clin. Pharmacol.
, vol.56
, pp. 805-811
-
-
Moore, K.H.P.1
Cass, L.M.2
Dallow, N.3
Hardman, T.C.4
Jones, A.5
Boyce, M.6
Prince, W.T.7
-
46
-
-
78349231814
-
-
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[1c]
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