-
1
-
-
33748621833
-
-
(a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. 1995, 34, 1348.
-
(1995)
Angew. Chem., Int. Ed.
, vol.34
, pp. 1348
-
-
Guram, A.S.1
Rennels, R.A.2
Buchwald, S.L.3
-
5
-
-
0003660996
-
-
Pergamon: Amsterdam
-
For examples of the decoration and construction of nitrogen-containing heterocycles via palladium-catalyzed C-C and C-N bond-forming reactions, see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Amsterdam, 2000.
-
(2000)
Palladium in Heterocyclic Chemistry
-
-
Li, J.J.1
Gribble, G.W.2
-
7
-
-
0034603363
-
-
For examples of the synthesis of nitrogen-containing heterocycles via the use of an intramolecular Pd-catalyzed amination, see the following references. (a) For indoles, see: Brown, J. A. Tetrahedron Lett. 2000, 41, 1623.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 1623
-
-
Brown, J.A.1
-
8
-
-
0029874188
-
-
(b) For indolines, 1,2,3,4-tetrahydroquinoline and 2,3,4,5-tetrahydro-1H- 1-benzazepine, see: Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525.
-
(1996)
Tetrahedron
, vol.52
, pp. 7525
-
-
Wolfe, J.P.1
Rennels, R.A.2
Buchwald, S.L.3
-
11
-
-
0034650815
-
-
(e) For phenazines, see: Emoto, T.; Kubosaki, N.; Yamagiwa, Y.; Kamikawa, T. Tetrahedron Lett. 2000, 41, 355.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 355
-
-
Emoto, T.1
Kubosaki, N.2
Yamagiwa, Y.3
Kamikawa, T.4
-
13
-
-
0000401303
-
-
(g) For pyrido[1,2-a]benzimidazole, see: Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 1505.
-
(1999)
J. Chem. Soc., Perkin Trans. 1
, pp. 1505
-
-
Iwaki, T.1
Yasuhara, A.2
Sakamoto, T.3
-
14
-
-
0037462378
-
-
(h) For oxazepine and thiazepine, see: Margolis, B. J.; Swidorski, J. J.; Rogers, B. N. J. Org. Chem. 2003, 68, 644.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 644
-
-
Margolis, B.J.1
Swidorski, J.J.2
Rogers, B.N.3
-
15
-
-
0038034710
-
-
For examples of tandem-catalyzed reactions that involve palladium-catalyzed C-N and C-C bond formation, see: (a) Yamazaki, K.; Nakamura, Y.; Kondo, Y. J. Org. Chem. 2003, 68, 6011.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 6011
-
-
Yamazaki, K.1
Nakamura, Y.2
Kondo, Y.3
-
16
-
-
10744229778
-
-
(b) Dajka-Halász, B.; Monsieurs, K.; Éliás, O.; Károlyházy, L.; Tapolcsányi, P.; Maes, B. U. W.; Riedl, Z.; Hajós, G.; Dommisse, R.; Lemière, G. L. F.; Košmrlj, J.; Mátyus, P. Tetrahedron 2004, 60, 2283.
-
(2004)
Tetrahedron
, vol.60
, pp. 2283
-
-
Dajka-Halász, B.1
Monsieurs, K.2
Éliás, O.3
Károlyházy, L.4
Tapolcsányi, P.5
Maes, B.U.W.6
Riedl, Z.7
Hajós, G.8
Dommisse, R.9
Lemière, G.L.F.10
Košmrlj, J.11
Mátyus, P.12
-
18
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0038249084
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-
Carbazoles and dithieno[3,2-b:2′,3′-d]pyrroles: (a) Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H.-Z.; Fujiki, M.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2051.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 2051
-
-
Nozaki, K.1
Takahashi, K.2
Nakano, K.3
Hiyama, T.4
Tang, H.-Z.5
Fujiki, M.6
Yamaguchi, S.7
Tamao, K.8
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19
-
-
12344280851
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-
(b) Kuwahara, A.; Nakano, K.; Nozaki, K. J. Org. Chem. 2005, 70, 413.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 413
-
-
Kuwahara, A.1
Nakano, K.2
Nozaki, K.3
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20
-
-
10044220843
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-
(c) Koeckelberghs, G.; De Cremer, L.; Vanormelingen, W.; Dehaen, W.; Verbiest, T.; Persoons, A.; Samyn, C. Tetrahedron 2005, 61, 687. Indoles:
-
(2005)
Tetrahedron
, vol.61
, pp. 687
-
-
Koeckelberghs, G.1
De Cremer, L.2
Vanormelingen, W.3
Dehaen, W.4
Verbiest, T.5
Persoons, A.6
Samyn, C.7
-
21
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-
(d) Willis, M. C.; Brace, G. N.; Holmes, I. P. Angew. Chem., Int. Ed. 2005, 44, 403.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 403
-
-
Willis, M.C.1
Brace, G.N.2
Holmes, I.P.3
-
22
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9444290796
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Dipyrido[1,2-a:3′,2′-d]imidazole and its benzo and aza analogues: Loones, K. T. J.; Maes, B. U. W.; Dommisse, R. A.; Lemière, G. L. F. Chem. Commun. 2004, 2466.
-
(2004)
Chem. Commun.
, pp. 2466
-
-
Loones, K.T.J.1
Maes, B.U.W.2
Dommisse, R.A.3
Lemière, G.L.F.4
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0036454157
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(a) Maes, B. U. W.; Loones, K. T. J.; Jonckers, T. H. M.; Lemière, G. L. F.; Dommisse, R. A.; Haemers, A. Synlett 2002, 1995.
-
(2002)
Synlett
, pp. 1995
-
-
Maes, B.U.W.1
Loones, K.T.J.2
Jonckers, T.H.M.3
Lemière, G.L.F.4
Dommisse, R.A.5
Haemers, A.6
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(b) Meyers, C.; Maes, B. U. W.; Loones, K. T. J.; Bal, G.; Lemière, G. L. F.; Dommisse, R. A. J. Org. Chem. 2004, 69, 6010.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 6010
-
-
Meyers, C.1
Maes, B.U.W.2
Loones, K.T.J.3
Bal, G.4
Lemière, G.L.F.5
Dommisse, R.A.6
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26
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31144444179
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note
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The C-2 chemoselective amination on 1 was confirmed via a C-Br hydrogenolysis reaction on the obtained N-(3-bromopyridin-2-yl) azaheteroarylamines.
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27
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31144444420
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Table A
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For details, see Supporting Information. (a) Table A.
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28
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31144452001
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Table B
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(b) Table B.
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29
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31144436720
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note
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(c) Temperature measured inside the vessel (fiber optic probe). Oil bath temperature = 160 °C.
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30
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31144436467
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Table C
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(d) For attempts to perform auto-tandem Cu-catalyzed double amination, see Table C.
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31
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0033597748
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Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 5575
-
-
Hartwig, J.F.1
Kawatsura, M.2
Hauck, S.I.3
Shaughnessy, K.H.4
Alcazar-Roman, L.M.5
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0033549829
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DTPB = 2-(di-tert-butylphosphanyl)biphenyl (JohnPhos), DCPB = 2-(dicyclohexylphosphanyl)biphenyl, DCPAB (DavePhos) = 2-dicyclohexylphosphanyl- 2′-(N,N-dimethylamino)biphenyl. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 2413
-
-
Wolfe, J.P.1
Buchwald, S.L.2
-
34
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(b) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 5327
-
-
Sadighi, J.P.1
Harris, M.C.2
Buchwald, S.L.3
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35
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0036643424
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IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene. Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69.
-
(2002)
J. Organomet. Chem.
, vol.653
, pp. 69
-
-
Hillier, A.C.1
Grasa, G.A.2
Viciu, M.S.3
Lee, H.M.4
Yang, C.5
Nolan, S.P.6
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36
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0345708168
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For recent reviews, see: (a) 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
-
39
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0037009958
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Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11684
-
-
Antilla, J.C.1
Klapars, A.2
Buchwald, S.L.3
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40
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31144477680
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note
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The intermolecular Pd-catalyzed amination of 1 with 2a was finished after 7 h, as judged by TLC and MS analysis.
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41
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0037201095
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Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Tetrahedron Lett. 2002, 43, 7143.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 7143
-
-
Kelkar, A.A.1
Patil, N.M.2
Chaudhari, R.V.3
-
42
-
-
0000264707
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-
Lu, J. Y.; Cabrera, B. R.; Wang, R. J.; Li, J. Inorg. Chem. 1998, 37, 4480.
-
(1998)
Inorg. Chem.
, vol.37
, pp. 4480
-
-
Lu, J.Y.1
Cabrera, B.R.2
Wang, R.J.3
Li, J.4
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43
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18244396643
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Only the dipyrido[1,2-a:2′,3′-d]imidazole skeleton and some substituted analogues are known: (a) Chezal, J. M.; Moreau, E.; Chavignon, O.; Gaumet, V.; Métin, J.; Blache, Y.; Diez, A.; Fradera, X.; Luque, J.; Teulade, J. C. Tetrahedron 2002, 58, 295.
-
(2002)
Tetrahedron
, vol.58
, pp. 295
-
-
Chezal, J.M.1
Moreau, E.2
Chavignon, O.3
Gaumet, V.4
Métin, J.5
Blache, Y.6
Diez, A.7
Fradera, X.8
Luque, J.9
Teulade, J.C.10
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45
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31144438811
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note
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Trace amounts (<5%) of dipyrido[1,2-a:3′,2′-d]imidazole and its benzo and aza analogues were also isolated. These regioisomers are presumably formed via tandem C-3 intermolecular and C-2 intramolecular metal-catalyzed amination.
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