-
3
-
-
29244491409
-
-
for the physiological activity of indole derivatives
-
c) T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761; for the physiological activity of indole derivatives,
-
(2005)
Nat. Prod. Rep
, vol.22
, pp. 761
-
-
Kawasaki, T.1
Higuchi, K.2
-
4
-
-
20944432343
-
-
for recent reports on the total synthesis of indole alkaloids, see: d
-
see: d) M. C. Van Zandt, M. L. Jones, D. E. Gunn, L. S. Geraci, J. H. Jones, D. R. Sawicki, J. Sredy, J. L. Jacot, A. T. DiCioccio, T. Petrova, A. Mitschler, A. D. Podjarny, J. Med. Chem. 2005, 48, 3141; for recent reports on the total synthesis of indole alkaloids,
-
(2005)
J. Med. Chem
, vol.48
, pp. 3141
-
-
Van Zandt, M.C.1
Jones, M.L.2
Gunn, D.E.3
Geraci, L.S.4
Jones, J.H.5
Sawicki, D.R.6
Sredy, J.7
Jacot, J.L.8
DiCioccio, A.T.9
Petrova, T.10
Mitschler, A.11
Podjarny, A.D.12
-
6
-
-
28744433443
-
-
f) P. S. Baran, C. A. Guerrero, B. D. Hafensteiner, N. B. Ambhaikar, Angew. Chem. 2005, 117, 3960;
-
(2005)
Angew. Chem
, vol.117
, pp. 3960
-
-
Baran, P.S.1
Guerrero, C.A.2
Hafensteiner, B.D.3
Ambhaikar, N.B.4
-
8
-
-
27544508842
-
-
g) T. Yamashita, N. Kawai, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2005, 127, 15038.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 15038
-
-
Yamashita, T.1
Kawai, N.2
Tokuyama, H.3
Fukuyama, T.4
-
9
-
-
22944454156
-
-
For reviews on methods for the synthesis of indoles, see: a
-
For reviews on methods for the synthesis of indoles, see: a) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873;
-
(2005)
Chem. Rev
, vol.105
, pp. 2873
-
-
Cacchi, S.1
Fabrizi, G.2
-
11
-
-
4444376920
-
-
see also the following reviews: c
-
see also the following reviews: c) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079;
-
(2004)
Chem. Rev
, vol.104
, pp. 3079
-
-
Alonso, F.1
Beletskaya, I.P.2
Yus, M.3
-
13
-
-
53249085567
-
-
for some recent indole syntheses, see: e
-
for some recent indole syntheses, see: e) M. Shen, B. E. Leslie, T. G. Driver, Angew. Chem. 2008, 120, 5134;
-
(2008)
Angew. Chem
, vol.120
, pp. 5134
-
-
Shen, M.1
Leslie, B.E.2
Driver, T.G.3
-
15
-
-
53249143742
-
-
f) J. Takaya, S. Udagawa, H. Kusama, N. Iwasawa, Angew. Chem. 2008, 120, 4984;
-
(2008)
Angew. Chem
, vol.120
, pp. 4984
-
-
Takaya, J.1
Udagawa, S.2
Kusama, H.3
Iwasawa, N.4
-
17
-
-
53249093493
-
-
g) T. Pei, C.-y. Chen, P. G. Dormer, I. W. Davies, Angew. Chem. 2008, 120, 4299;
-
(2008)
Angew. Chem
, vol.120
, pp. 4299
-
-
Pei, T.1
Chen, C.-Y.2
Dormer, P.G.3
Davies, I.W.4
-
19
-
-
41549087119
-
-
h) K. Alex, A. Tillack, N. Schwarz, M. Beller, Angew. Chem. 2008, 120, 2337;
-
(2008)
Angew. Chem
, vol.120
, pp. 2337
-
-
Alex, K.1
Tillack, A.2
Schwarz, N.3
Beller, M.4
-
23
-
-
36849030278
-
-
E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318.
-
(2007)
Chem. Rev
, vol.107
, pp. 5318
-
-
Beccalli, E.M.1
Broggini, G.2
Martinelli, M.3
Sottocornola, S.4
-
24
-
-
53249155699
-
-
For the use of indole derivatives in cross-dehydrogenative coupling (CDC) reactions, see: a) T. Tsuchimoto, Y. Ozawa, R. Negoro, E. Shirakawa, Y. Kawakami, Angew. Chem. 2004, 116, 4327;
-
For the use of indole derivatives in cross-dehydrogenative coupling (CDC) reactions, see: a) T. Tsuchimoto, Y. Ozawa, R. Negoro, E. Shirakawa, Y. Kawakami, Angew. Chem. 2004, 116, 4327;
-
-
-
-
28
-
-
34547960227
-
-
d) T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137;
-
(2007)
Org. Lett
, vol.9
, pp. 3137
-
-
Dwight, T.A.1
Rue, N.R.2
Charyk, D.3
Josselyn, R.4
DeBoef, B.5
-
29
-
-
34249936878
-
-
for a remarkable CDC of indoles with unfunctionalized benzene derivatives, see: e D. R. Stuart, K. Fagnou, Science 2007, 316, 1172;
-
for a remarkable CDC of indoles with unfunctionalized benzene derivatives, see: e) D. R. Stuart, K. Fagnou, Science 2007, 316, 1172;
-
-
-
-
30
-
-
35048815950
-
-
f) D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 12072
-
-
Stuart, D.R.1
Villemure, E.2
Fagnou, K.3
-
31
-
-
0034867872
-
-
For CDCs of other substrates, see: a
-
For CDCs of other substrates, see: a) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
-
(2001)
Acc. Chem. Res
, vol.34
, pp. 633
-
-
Jia, C.1
Kitamura, T.2
Fujiwara, Y.3
-
32
-
-
53249102895
-
-
b) K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 14047;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 14047
-
-
Hull, K.L.1
Lanni, E.L.2
Sanford, M.S.3
-
34
-
-
0037181051
-
-
d) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586;
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 1586
-
-
Boele, M.D.K.1
van Strijdonck, G.P.F.2
de Vries, A.H.M.3
Kamer, P.C.J.4
de Vries, J.G.5
van Leeuwen, P.W.N.M.6
-
35
-
-
4544315557
-
-
e) M. Dams, D. E. De Vos, S. Celen, P. A. Jacobs, Angew. Chem. 2003, 115, 3636;
-
(2003)
Angew. Chem
, vol.115
, pp. 3636
-
-
Dams, M.1
De Vos, D.E.2
Celen, S.3
Jacobs, P.A.4
-
37
-
-
1942521272
-
-
f) K. Masui, H. Ikegami, A. Mori, J. Am. Chem. Soc. 2004, 126, 5074;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 5074
-
-
Masui, K.1
Ikegami, H.2
Mori, A.3
-
41
-
-
54849172300
-
-
i) Z. Li, L. Cao, C.-J. Li, Angew. Chem. 2007, 119, 6625;
-
(2007)
Angew. Chem
, vol.119
, pp. 6625
-
-
Li, Z.1
Cao, L.2
Li, C.-J.3
-
43
-
-
33846918696
-
-
a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
-
(2007)
Chem. Rev
, vol.107
, pp. 174
-
-
Alberico, D.1
Scott, M.E.2
Lautens, M.3
-
44
-
-
20544450502
-
-
2nd ed, Eds, A. de Meijere, F. Diederich, Wiley-VCH, Weinheim
-
b) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
-
-
-
45
-
-
0036589259
-
-
c) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359.
-
(2002)
Chem. Rev
, vol.102
, pp. 1359
-
-
Hassan, J.1
Sevignon, M.2
Gozzi, C.3
Schulz, E.4
Lemaire, M.5
-
46
-
-
0028893764
-
-
a) B. Åkermark, J. D. Oslob, U. Heuschert, Tetrahedron Lett. 1995, 36, 1325;
-
(1995)
Tetrahedron Lett
, vol.36
, pp. 1325
-
-
Åkermark, B.1
Oslob, J.D.2
Heuschert, U.3
-
47
-
-
0032818056
-
-
b) H. Hagelin, J. D. Oslob, B. Åkermark, Chem. Eur. J. 1999, 5, 2413;
-
(1999)
Chem. Eur. J
, vol.5
, pp. 2413
-
-
Hagelin, H.1
Oslob, J.D.2
Åkermark, B.3
-
50
-
-
0032487805
-
-
e) H.-J. Knölker, K. R. Reddy, A. Wagner, Tetrahedron Lett. 1998, 39, 8267;
-
(1998)
Tetrahedron Lett
, vol.39
, pp. 8267
-
-
Knölker, H.-J.1
Reddy, K.R.2
Wagner, A.3
-
52
-
-
24644504824
-
-
g) S. Agarwal, S. Cämmerer, S. Filali, W. Fröhner, J. Knöll, M. P. Krahl, K. R. Reddy, H.-J. Knölker, Curr. Org. Chem. 2005, 9, 1601.
-
(2005)
Curr. Org. Chem
, vol.9
, pp. 1601
-
-
Agarwal, S.1
Cämmerer, S.2
Filali, S.3
Fröhner, W.4
Knöll, J.5
Krahl, M.P.6
Reddy, K.R.7
Knölker, H.-J.8
-
53
-
-
33847801634
-
-
a) B. Åkermark, L. Eberson, E. Jonsson, E. Pettersson, J. Org. Chem. 1975, 40, 1365;
-
(1975)
J. Org. Chem
, vol.40
, pp. 1365
-
-
Åkermark, B.1
Eberson, L.2
Jonsson, E.3
Pettersson, E.4
-
55
-
-
33747876110
-
-
c) M. P. Krahl, A. Jäger, T. Krause, H.-J. Knölker, Org. Biomol. Chem. 2006, 4, 3215;
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 3215
-
-
Krahl, M.P.1
Jäger, A.2
Krause, T.3
Knölker, H.-J.4
-
56
-
-
0037163272
-
-
d) I. C. F. R. Ferreira, M.-J. R. P. Queiroz, G. Kirsch, Tetrahedron 2002, 58, 7943;
-
(2002)
Tetrahedron
, vol.58
, pp. 7943
-
-
Ferreira, I.C.F.R.1
Queiroz, M.-J.R.P.2
Kirsch, G.3
-
57
-
-
35748974155
-
-
e) T. Watanabe, S. Ueda, S. Inuki, S. Oishi, N. Fujii, H. Ohno, Chem. Commun. 2007, 4516.
-
(2007)
Chem. Commun
, pp. 4516
-
-
Watanabe, T.1
Ueda, S.2
Inuki, S.3
Oishi, S.4
Fujii, N.5
Ohno, H.6
-
58
-
-
0001304357
-
-
For a palladium-catalyzed cyclization of a single N-aryl- substituted (cyclic) enaminone under neutral conditions in 31% yield, see: a) H. Iida, Y. Yuasa, C. Kibayashi, J. Org. Chem. 1980, 45, 2938;
-
For a palladium-catalyzed cyclization of a single N-aryl- substituted (cyclic) enaminone under neutral conditions in 31% yield, see: a) H. Iida, Y. Yuasa, C. Kibayashi, J. Org. Chem. 1980, 45, 2938;
-
-
-
-
59
-
-
0001196247
-
-
for a two-step synthesis of indoles by anodic oxidation of an enaminone in 35% yield, and additional cyclizations, see: b W. Eilenberg, H. J. Schäfer, Tetrahedron Lett. 1984, 25, 5023;
-
for a two-step synthesis of indoles by anodic oxidation of an enaminone in 35% yield, and additional cyclizations, see: b) W. Eilenberg, H. J. Schäfer, Tetrahedron Lett. 1984, 25, 5023;
-
-
-
-
60
-
-
16544375833
-
-
for photochemical cyclizations for the synthesis of tricyclic ketoindoles, see: c
-
for photochemical cyclizations for the synthesis of tricyclic ketoindoles, see: c) P.-J. Aragon, A.-D. Yapi, F. Pinguet, J.-M. Chezal, J.-C. Teulade, J.-P. Chapat, Y. Blache, Chem. Pharm. Bull. 2004, 52, 659;
-
(2004)
Chem. Pharm. Bull
, vol.52
, pp. 659
-
-
Aragon, P.-J.1
Yapi, A.-D.2
Pinguet, F.3
Chezal, J.-M.4
Teulade, J.-C.5
Chapat, J.-P.6
Blache, Y.7
-
61
-
-
0036746852
-
-
d) C. Tietcheu, C. Garcia, D. Gardette, D. Dugat, J.-C. Gramain, J. Heterocycl. Chem. 2002, 39, 965.
-
(2002)
J. Heterocycl. Chem
, vol.39
, pp. 965
-
-
Tietcheu, C.1
Garcia, C.2
Gardette, D.3
Dugat, D.4
Gramain, J.-C.5
-
62
-
-
53249107322
-
-
[5d]
-
[5d]
-
-
-
-
63
-
-
0035128727
-
-
For Suzuki-Miyaura reactions of chloroindoles, see: a
-
For Suzuki-Miyaura reactions of chloroindoles, see: a) A. FOrstner, A. Leitner, Synlett 2001, 290;
-
(2001)
Synlett
, pp. 290
-
-
FOrstner, A.1
Leitner, A.2
-
64
-
-
33745721267
-
-
b) N. Kudo, M. Perseghini, G. C. Fu, Angew. Chem. 2006, 118, 1304;
-
(2006)
Angew. Chem
, vol.118
, pp. 1304
-
-
Kudo, N.1
Perseghini, M.2
Fu, G.C.3
-
66
-
-
53249128629
-
-
Bromo-substituted indoles can also be formed; however, a significant amount of the debrominated indole product is also obtained. The optimization of this reaction will be described at a later stage
-
Bromo-substituted indoles can also be formed; however, a significant amount of the debrominated indole product is also obtained. The optimization of this reaction will be described at a later stage.
-
-
-
-
67
-
-
53249140072
-
-
As an example of the value of this method, we quote for one transformation the cost of purchasing the starting materials and the product in 99% purity from Sigma-Aldrich: aniline: 1 L/€24; ethyl acetoacetate: 1 kg/€37; ethyl-2-methylindole-3-carboxylate (2u): 1 g/€60.60.
-
As an example of the value of this method, we quote for one transformation the cost of purchasing the starting materials and the product in 99% purity from Sigma-Aldrich: aniline: 1 L/€24; ethyl acetoacetate: 1 kg/€37; ethyl-2-methylindole-3-carboxylate (2u): 1 g/€60.60.
-
-
-
-
68
-
-
31544466241
-
-
Z.-H. Zhang, L. Yin, Y.-M. Wang, Adv. Synth. Catal. 2006, 348, 184.
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 184
-
-
Zhang, Z.-H.1
Yin, L.2
Wang, Y.-M.3
-
69
-
-
0037020620
-
-
a) M. E. F. Braibante, H. T. S. Braibante, C. C. Costa, D. B. Martins, Tetrahedron Lett. 2002, 43, 8079;
-
(2002)
Tetrahedron Lett
, vol.43
, pp. 8079
-
-
Braibante, M.E.F.1
Braibante, H.T.S.2
Costa, C.C.3
Martins, D.B.4
-
70
-
-
0028141787
-
-
b) M. E. F. Braibante, H. S. Braibante, L. Missio, A. Andricopulo, Synthesis 1994, 898.
-
(1994)
Synthesis
, pp. 898
-
-
Braibante, M.E.F.1
Braibante, H.S.2
Missio, L.3
Andricopulo, A.4
-
71
-
-
41149138082
-
-
H. Ge, M. J. Niphakis, G. I. Georg, J. Am. Chem. Soc. 2008, 130, 3708.
-
(2008)
J. Am. Chem. Soc
, vol.130
, pp. 3708
-
-
Ge, H.1
Niphakis, M.J.2
Georg, G.I.3
-
72
-
-
53249089875
-
-
An initial olefin-palladium π complex should also be considered; see: F. Glorius, Angew. Chem. 2004, 116, 3444;
-
An initial olefin-palladium π complex should also be considered; see: F. Glorius, Angew. Chem. 2004, 116, 3444;
-
-
-
-
73
-
-
4544236676
-
-
and references therein
-
Angew. Chem. Int. Ed. 2004, 43, 3364, and references therein.
-
(2004)
Angew. Chem. Int. Ed
, vol.43
, pp. 3364
-
-
-
74
-
-
0037266893
-
-
A. M. Echavarren, B. Gómez-Lor, J. J. González, Ó. de Frutos, Synlett 2003, 585.
-
(2003)
Synlett
, pp. 585
-
-
Echavarren, A.M.1
Gómez-Lor, B.2
González, J.J.3
de Frutos, O.4
-
75
-
-
31944442069
-
-
a) D. García-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066;
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 1066
-
-
García-Cuadrado, D.1
Braga, A.A.C.2
Maseras, F.3
Echavarren, A.M.4
-
76
-
-
34249793676
-
-
b) D. García-Cuadrado, P. de Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2007, 129, 6880;
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 6880
-
-
García-Cuadrado, D.1
de Mendoza, P.2
Braga, A.A.C.3
Maseras, F.4
Echavarren, A.M.5
-
78
-
-
0037771628
-
-
Some alternative, though less likely mechanisms, may be considered; for a Heck carbopalladation, see: a
-
Some alternative, though less likely mechanisms, may be considered; for a Heck carbopalladation, see: a) C. C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 1639;
-
(2002)
Angew. Chem
, vol.114
, pp. 1639
-
-
Hughes, C.C.1
Trauner, D.2
-
80
-
-
0037562071
-
-
b) B. Glover, K. A. Harvey, B. Liu, M. J. Sharp, M. F. Tymoschenko, Org. Lett. 2003, 5, 301;
-
(2003)
Org. Lett
, vol.5
, pp. 301
-
-
Glover, B.1
Harvey, K.A.2
Liu, B.3
Sharp, M.J.4
Tymoschenko, M.F.5
-
81
-
-
18744368757
-
-
IV intermediate, see: c A. J. Mota, A. Dedieu, C. Bour, J. Suffert, J. Am. Chem. Soc. 2005, 127, 7171;
-
IV intermediate, see: c) A. J. Mota, A. Dedieu, C. Bour, J. Suffert, J. Am. Chem. Soc. 2005, 127, 7171;
-
-
-
-
82
-
-
53249134242
-
-
II species, see: d J. Cámpora, E. Gutiérrez-Puebla, J. A. López, A. Monge, P. Palma, D. del Río, E. Carmona, Angew. Chem. 2001, 113, 3753;
-
II species, see: d) J. Cámpora, E. Gutiérrez-Puebla, J. A. López, A. Monge, P. Palma, D. del Río, E. Carmona, Angew. Chem. 2001, 113, 3753;
-
-
-
-
84
-
-
53249153232
-
-
The following reactivity order was found for para-substituted aniline substrates: Cl > H ≈ Me > OMe. Details are provided in the Supporting Information.
-
The following reactivity order was found for para-substituted aniline substrates: Cl > H ≈ Me > OMe. Details are provided in the Supporting Information.
-
-
-
-
85
-
-
26844453646
-
-
For examples, see: a
-
For examples, see: a) N. Lachance, M. April, M.-A. Joly, Synthesis 2005, 2571;
-
(2005)
Synthesis
, pp. 2571
-
-
Lachance, N.1
April, M.2
Joly, M.-A.3
-
87
-
-
0030908560
-
-
c) C. Chen, D. R. Lieberman, R. D. Larsen, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1997, 62, 2676.
-
(1997)
J. Org. Chem
, vol.62
, pp. 2676
-
-
Chen, C.1
Lieberman, D.R.2
Larsen, R.D.3
Verhoeven, T.R.4
Reider, P.J.5
|