-
1
-
-
2042507954
-
-
For reviews of the palladium-catalyzed Suzuki-Miyaura coupling reactions, see: a
-
For reviews of the palladium-catalyzed Suzuki-Miyaura coupling reactions, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
-
(1995)
Chem. Rev
, vol.95
, pp. 2457-2483
-
-
Miyaura, N.1
Suzuki, A.2
-
4
-
-
0037175592
-
-
d) S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695;
-
(2002)
Tetrahedron
, vol.58
, pp. 9633-9695
-
-
Kotha, S.1
Lahiri, K.2
Kashinath, D.3
-
5
-
-
68949127793
-
-
F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 15, 24192440;
-
e) F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 15, 24192440;
-
-
-
-
8
-
-
0036589259
-
-
J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1470.
-
(2002)
Chem. Rev
, vol.102
, pp. 1359-1470
-
-
Hassan, J.1
Sevignon, M.2
Gozzi, C.3
Schulz, E.4
Lemaire, M.5
-
9
-
-
0000397168
-
-
S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701;
-
(2001)
Angew. Chem
, vol.113
, pp. 4676-4701
-
-
Chemler, S.R.1
Trauner, D.2
Danishefsky, S.J.3
-
10
-
-
0035905441
-
-
Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
-
(2001)
Angew. Chem. Int. Ed
, vol.40
, pp. 4544-4568
-
-
-
11
-
-
0036643471
-
-
N. Yasuda, J. Organomet. Chem. 2002, 253, 279-/287.
-
N. Yasuda, J. Organomet. Chem. 2002, 253, 279-/287.
-
-
-
-
12
-
-
34249068477
-
-
a) L. Liao, A. Cirpan, Q. Chu, F. E. Karasz, Y. Pang, J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 2048-2058.
-
(2007)
J. Polym. Sci. Part A: Polym. Chem
, vol.45
, pp. 2048-2058
-
-
Liao, L.1
Cirpan, A.2
Chu, Q.3
Karasz, F.E.4
Pang, Y.5
-
13
-
-
11144323895
-
-
For complete reviews of the state of the art, see: a
-
For complete reviews of the state of the art, see: a) C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254;
-
(2004)
Chem. Rev
, vol.104
, pp. 6217-6254
-
-
Bolm, C.1
Legros, J.2
Le Paih, J.3
Zani, L.4
-
14
-
-
54849171100
-
-
b) S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367;
-
(2008)
Angew. Chem
, vol.120
, pp. 3363-3367
-
-
Enthaler, S.1
Junge, K.2
Beller, M.3
-
15
-
-
50049109778
-
-
Angew. Chem. Int. Ed. 2008, 47, 3317-3321;
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 3317-3321
-
-
-
16
-
-
44349129755
-
-
A. Correa, O. Garcia Mancheno, C. Bolm, Chem. Soc. Rev., 2008, 37, 11081117.
-
c) A. Correa, O. Garcia Mancheno, C. Bolm, Chem. Soc. Rev., 2008, 37, 11081117.
-
-
-
-
17
-
-
59949090015
-
-
a) A. M. Tondreau, E. Lobkovsky, P.J. Chirik, Org. Lett. 2008, 10, 2789-2792;
-
(2008)
Org. Lett
, vol.10
, pp. 2789-2792
-
-
Tondreau, A.M.1
Lobkovsky, E.2
Chirik, P.J.3
-
18
-
-
53549121829
-
-
b) N. S. Shaikh, S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 2531-2535;
-
(2008)
Angew. Chem
, vol.120
, pp. 2531-2535
-
-
Shaikh, N.S.1
Enthaler, S.2
Junge, K.3
Beller, M.4
-
19
-
-
42449118890
-
-
Angew. Chem. Int. Ed. 2008, 47, 2497-2501;
-
(2008)
Angew. Chem. Int. Ed
, vol.47
, pp. 2497-2501
-
-
-
20
-
-
40949106167
-
-
c) F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M. K. Tse, M. Beller, Angew. Chem. 2007, 119, 7431-7435;
-
(2007)
Angew. Chem
, vol.119
, pp. 7431-7435
-
-
Gelalcha, F.G.1
Bitterlich, B.2
Anilkumar, G.3
Tse, M.K.4
Beller, M.5
-
21
-
-
34948835849
-
-
Angew. Chem. Int. Ed 2007, 46, 7293-7296;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 7293-7296
-
-
-
22
-
-
38349096219
-
-
N. S. Shaikh, K. Junge, M. Beller, Org. Lett. 2007, 9, 54295432;
-
d) N. S. Shaikh, K. Junge, M. Beller, Org. Lett. 2007, 9, 54295432;
-
-
-
-
25
-
-
55049110729
-
-
a) F. Shi, M. K. Tse, Z. Li, M. Beller, Chem. Eur. J. 2008, 14, 8793-8797;
-
(2008)
Chem. Eur. J
, vol.14
, pp. 8793-8797
-
-
Shi, F.1
Tse, M.K.2
Li, Z.3
Beller, M.4
-
27
-
-
68949143762
-
-
c) C. Pa van, J. Legros, C. Bolm, Adv. Synth. Catal. 2005, 347, 703705;
-
(2005)
Adv. Synth. Catal
, vol.347
, pp. 703705
-
-
Pa van, C.1
Legros, J.2
Bolm, C.3
-
30
-
-
68949118566
-
-
Angew. Chem. Int. Ed. 2004, 43, 42254228;
-
Angew. Chem. Int. Ed. 2004, 43, 42254228;
-
-
-
-
32
-
-
68949084027
-
-
Angew. Chem. Int. Ed. 2003, 42, 54875489;
-
Angew. Chem. Int. Ed. 2003, 42, 54875489;
-
-
-
-
33
-
-
54849172300
-
-
g) Z. Li, L. Cao, C.-J. Li, Angew. Chem. 2007, 119, 6625-6627;
-
(2007)
Angew. Chem
, vol.119
, pp. 6625-6627
-
-
Li, Z.1
Cao, L.2
Li, C.-J.3
-
34
-
-
68949127792
-
-
Angew. Chem. Int. Ed. 2007, 46, 65056507;
-
Angew. Chem. Int. Ed. 2007, 46, 65056507;
-
-
-
-
35
-
-
59049103808
-
-
h) Z. Li, R. Yu, H. Li, Angew. Chem. 2008, 120, 7607-7610;
-
(2008)
Angew. Chem
, vol.120
, pp. 7607-7610
-
-
Li, Z.1
Yu, R.2
Li, H.3
-
36
-
-
68949136218
-
-
Angew. Chem. Int. Ed. 2008, 47, 74977500.
-
Angew. Chem. Int. Ed. 2008, 47, 74977500.
-
-
-
-
37
-
-
53849113359
-
-
a) B. Bitterlich, K. Schroeder, M. K. Tse, M. Beller, Eur. J. Org. Chem. 2008, 29, 4867-4870;
-
(2008)
Eur. J. Org. Chem
, vol.29
, pp. 4867-4870
-
-
Bitterlich, B.1
Schroeder, K.2
Tse, M.K.3
Beller, M.4
-
38
-
-
53849141215
-
-
b) F. G. Gelalcha, G. Anilkumar, M. K. Tse, A. Bruckner, M. Beller, Chem. Eur. J. 2008, 14, 7687-7698;
-
(2008)
Chem. Eur. J
, vol.14
, pp. 7687-7698
-
-
Gelalcha, F.G.1
Anilkumar, G.2
Tse, M.K.3
Bruckner, A.4
Beller, M.5
-
39
-
-
40949106167
-
-
c) F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M. K. Tse, M. Beller, Angew. Chem. 2007, 119, 7431-7435;
-
(2007)
Angew. Chem
, vol.119
, pp. 7431-7435
-
-
Gelalcha, F.G.1
Bitterlich, B.2
Anilkumar, G.3
Tse, M.K.4
Beller, M.5
-
40
-
-
34948835849
-
-
Angew. Chem. Int. Ed. 2007, 46, 7293-7296;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 7293-7296
-
-
-
41
-
-
34547657722
-
-
d) K. Schroeder, X. Tong, B. Bitterlich, M. K. Tse, F. G. Gelalcha, A. Brueckner, M. Beller, Tetrahedron Lett. 2007, 48, 6339-6342;
-
(2007)
Tetrahedron Lett
, vol.48
, pp. 6339-6342
-
-
Schroeder, K.1
Tong, X.2
Bitterlich, B.3
Tse, M.K.4
Gelalcha, F.G.5
Brueckner, A.6
Beller, M.7
-
42
-
-
34249856683
-
-
e) B. Bitterlich, G. Anilkumar, F. G. Gelalcha, B. Spilker, A. Grotevendt, R. Jackstell, M. K. Tse, M. Beller, Chem. Asian J. 2007, 2, 521-529;
-
(2007)
Chem. Asian J
, vol.2
, pp. 521-529
-
-
Bitterlich, B.1
Anilkumar, G.2
Gelalcha, F.G.3
Spilker, B.4
Grotevendt, A.5
Jackstell, R.6
Tse, M.K.7
Beller, M.8
-
43
-
-
33845974070
-
-
f) G. Anilkumar, B. Bitterlich, F.G. Gelalcha, M. K. Tse, M. Beller, Chem. Commun. 2007, 289-291.
-
(2007)
Chem. Commun
, pp. 289-291
-
-
Anilkumar, G.1
Bitterlich, B.2
Gelalcha, F.G.3
Tse, M.K.4
Beller, M.5
-
45
-
-
33750600572
-
-
b) S. Enthaler, B. Hagemann, G. Erre, K. Junge, M. Beller, Chem. Asian J. 2006, 1, 598-604;
-
(2006)
Chem. Asian J
, vol.1
, pp. 598-604
-
-
Enthaler, S.1
Hagemann, B.2
Erre, G.3
Junge, K.4
Beller, M.5
-
46
-
-
6444222176
-
-
c) S. C. Bart, E. Lobkovsky, P. J. Chirik, J. Am. Chem. Soc. 2004, 126, 13794-13807.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 13794-13807
-
-
Bart, S.C.1
Lobkovsky, E.2
Chirik, P.J.3
-
47
-
-
0000689303
-
-
For pioneering examples of iron-catalyzed cross-coupling using Grignard reagents, see: a
-
For pioneering examples of iron-catalyzed cross-coupling using Grignard reagents, see: a) M. Tamura, J. K. Kochi, J. Am. Chem. Soc. 1971, 93, 1487-1489;
-
(1971)
J. Am. Chem. Soc
, vol.93
, pp. 1487-1489
-
-
Tamura, M.1
Kochi, J.K.2
-
54
-
-
0000957922
-
-
For recent examples of iron-catalyzed cross-coupling using Grignard reagents, see : a G. Molander, B. Rahn, D. C. Shubert, S. E. Bonde, Tetrahedron Lett. 1983, 24, 5449-5452;
-
For recent examples of iron-catalyzed cross-coupling using Grignard reagents, see : a) G. Molander, B. Rahn, D. C. Shubert, S. E. Bonde, Tetrahedron Lett. 1983, 24, 5449-5452;
-
-
-
-
56
-
-
0035212248
-
-
c) W. Dohle, F. Kopp, G. Cahiez, P. Knöchel, Synlett 2001, 1901-1904;
-
(2001)
Synlett
, pp. 1901-1904
-
-
Dohle, W.1
Kopp, F.2
Cahiez, G.3
Knöchel, P.4
-
57
-
-
0037146041
-
-
d) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863;
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 13856-13863
-
-
Fürstner, A.1
Leitner, A.2
Méndez, M.3
Krause, H.4
-
59
-
-
0037083916
-
-
Angew. Chem. Int. Ed. 2002, 41, 609-612;
-
(2002)
Angew. Chem. Int. Ed
, vol.41
, pp. 609-612
-
-
-
61
-
-
0344012926
-
-
Angew. Chem. Int. Ed. 2003, 42, 5355-5357;
-
(2003)
Angew. Chem. Int. Ed
, vol.42
, pp. 5355-5357
-
-
-
63
-
-
0037455149
-
-
Angew. Chem. Int. Ed. 2003, 42, 308-311;
-
(2003)
Angew. Chem. Int. Ed
, vol.42
, pp. 308-311
-
-
-
65
-
-
4544274092
-
-
i) A. Fürstner, D. de Souza, L. Parra-Rapado, J. T Jensen, Angew. Chem. 2003, 115, 5516-5518;
-
(2003)
Angew. Chem
, vol.115
, pp. 5516-5518
-
-
Fürstner, A.1
de Souza, D.2
Parra-Rapado, L.3
Jensen, J.T.4
-
66
-
-
0344875684
-
-
Angew. Chem. Int. Ed. 2003, 42, 5358-5360;
-
(2003)
Angew. Chem. Int. Ed
, vol.42
, pp. 5358-5360
-
-
-
68
-
-
2442656574
-
-
k) B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner. J. Org. Chem. 2004, 69, 3943-3949;
-
(2004)
J. Org. Chem
, vol.69
, pp. 3943-3949
-
-
Scheiper, B.1
Bonnekessel, M.2
Krause, H.3
Fürstner, A.4
-
69
-
-
2442680336
-
-
l) G. Seidel, D. Laurich, A. Fürstner, J. Org. Chem. 2004, 69, 3950-3952;
-
(2004)
J. Org. Chem
, vol.69
, pp. 3950-3952
-
-
Seidel, G.1
Laurich, D.2
Fürstner, A.3
-
71
-
-
68949115041
-
-
Angew. Chem. Int. Ed. 2004, 43, 39553957;
-
Angew. Chem. Int. Ed. 2004, 43, 39553957;
-
-
-
-
72
-
-
1642361256
-
-
n) M. Nakamura, K. Matsuo, S. Ito, E. Naka-mura, J. Am. Chem. Soc. 2004, 126, 3686-3687;
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 3686-3687
-
-
Nakamura, M.1
Matsuo, K.2
Ito, S.3
Naka-mura, E.4
-
74
-
-
11244292013
-
-
p) R. B. Bedford, D.W. Bruce, R. M. Frost, J.W. Goodby, M. Hird, Chem. Commun. 2004, 2822-2823;
-
(2004)
Chem. Commun
, pp. 2822-2823
-
-
Bedford, R.B.1
Bruce, D.W.2
Frost, R.M.3
Goodby, J.W.4
Hird, M.5
-
75
-
-
19544373479
-
-
q) G. Cahiez, C. Chaboche, F. Mahuteau-Betzer, M. Ahr, Org. Lett. 2005, 7, 1943-1946;
-
(2005)
Org. Lett
, vol.7
, pp. 1943-1946
-
-
Cahiez, G.1
Chaboche, C.2
Mahuteau-Betzer, F.3
Ahr, M.4
-
76
-
-
25144465934
-
-
r) R. B. Bedford, D. W. Bruce, R. M. Frost, M. Hird, Chem. Commun. 2005, 4161-4163;
-
(2005)
Chem. Commun
, pp. 4161-4163
-
-
Bedford, R.B.1
Bruce, D.W.2
Frost, R.M.3
Hird, M.4
-
77
-
-
32144461712
-
-
s) R. B. Bedford, M. Betham, D.W. Bruce, A. A. Danopoulos, R. M. Frost, M. Hird, J. Org. Chem. 2006, 71, 1104-1110;
-
(2006)
J. Org. Chem
, vol.71
, pp. 1104-1110
-
-
Bedford, R.B.1
Betham, M.2
Bruce, D.W.3
Danopoulos, A.A.4
Frost, R.M.5
Hird, M.6
-
78
-
-
68949127791
-
-
G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 44424444;
-
t) G. Cahiez, V. Habiak, C. Duplais, A. Moyeux, Angew. Chem. 2007, 119, 44424444;
-
-
-
-
79
-
-
34447275675
-
-
Angew. Chem. Int. Ed. 2007, 46, 4364-4366;
-
(2007)
Angew. Chem. Int. Ed
, vol.46
, pp. 4364-4366
-
-
-
81
-
-
48849106777
-
-
v) G. Cahiez, V. Habiak, O. Gager, Org. Lett. 2008, 10, 2389-2392;
-
(2008)
Org. Lett
, vol.10
, pp. 2389-2392
-
-
Cahiez, G.1
Habiak, V.2
Gager, O.3
-
83
-
-
58649099580
-
-
For an example of iron-catalyzed cross-coupling using organozinc reagents, see: a
-
For an example of iron-catalyzed cross-coupling using organozinc reagents, see: a) R. B. Bedford, M. Huwe, M. C. Wilkinson, Chem. Commun. 2009, 600-602;
-
(2009)
Chem. Commun
, pp. 600-602
-
-
Bedford, R.B.1
Huwe, M.2
Wilkinson, M.C.3
-
84
-
-
68949087194
-
-
b) G. Cahiez, L. Foulgoc, A. Moyeux, Angew. Chem. 2009, 727, 3013 -3016;
-
(2009)
Angew. Chem
, vol.727
, pp. 3013-3016
-
-
Cahiez, G.1
Foulgoc, L.2
Moyeux, A.3
-
85
-
-
70349782138
-
-
Angew. Chem. Int. Ed. 2009, 48, 2969-2972.
-
(2009)
Angew. Chem. Int. Ed
, vol.48
, pp. 2969-2972
-
-
-
86
-
-
34250838230
-
-
For examples of iron-catalyzed cross-coupling using organocopper reagents, see, a C. C. Kofink, B. Blank, S. Pagano, N. Götz, P. Knöchel, Chem. Commun. 2007, 1954-1956;
-
For examples of iron-catalyzed cross-coupling using organocopper reagents, see : a) C. C. Kofink, B. Blank, S. Pagano, N. Götz, P. Knöchel, Chem. Commun. 2007, 1954-1956;
-
-
-
-
87
-
-
18844394227
-
-
b) I. Sapountzis, W Lin, C. Kofink, C. Despotopoulou, P. Knochel, Angew. Chem. 2005, 117, 1682-1685;
-
(2005)
Angew. Chem
, vol.117
, pp. 1682-1685
-
-
Sapountzis, I.1
Lin, W.2
Kofink, C.3
Despotopoulou, C.4
Knochel, P.5
-
88
-
-
68949112752
-
-
Angew. Chem. Int. Ed. 2005, 44, 16541657;
-
Angew. Chem. Int. Ed. 2005, 44, 16541657;
-
-
-
-
89
-
-
68949123383
-
-
P. Knochel, I. Sapountzis, T. Korn, W. Lin, C. Kofink, Ger. Offen. DE102004049508, 2006.
-
c) P. Knochel, I. Sapountzis, T. Korn, W. Lin, C. Kofink, Ger. Offen. DE102004049508, 2006.
-
-
-
-
90
-
-
0029970234
-
-
For examples of iron-catalyzed cross-coupling using organomanganese reagents, see: a G. Cahiez, S. Marquais, Tetrahedron Lett. 1996, 37, 1773-1776;
-
For examples of iron-catalyzed cross-coupling using organomanganese reagents, see: a) G. Cahiez, S. Marquais, Tetrahedron Lett. 1996, 37, 1773-1776;
-
-
-
-
92
-
-
53149090170
-
-
T. Kylmälä, A. Valkonen, K. Rissanen, Y. Xu, R. Franzén, Tetrahedron Lett. 2008, 49, 6679-6681.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 6679-6681
-
-
Kylmälä, T.1
Valkonen, A.2
Rissanen, K.3
Xu, Y.4
Franzén, R.5
-
94
-
-
60849134294
-
-
X.-F. Wu, D. Bezier, C. Darcel, Adv. Synth. Catal 2009, 351, 367-370.
-
(2009)
Adv. Synth. Catal
, vol.351
, pp. 367-370
-
-
Wu, X.-F.1
Bezier, D.2
Darcel, C.3
-
95
-
-
68949092850
-
-
X.-F. Wu, C. Vovard-Le Bray, L. Bechki, C. Darcel, Tetrahedron 2009, doi: 10.1016/j.tet.2009.07.29>.
-
X.-F. Wu, C. Vovard-Le Bray, L. Bechki, C. Darcel, Tetrahedron 2009, doi: 10.1016/j.tet.2009.07.29>.
-
-
-
-
96
-
-
49149123814
-
-
Y. Guo, D. J. Young, T. S. A. Hor, Tetrahedron Lett. 2008, 49, 5620-5621.
-
(2008)
Tetrahedron Lett
, vol.49
, pp. 5620-5621
-
-
Guo, Y.1
Young, D.J.2
Hor, T.S.A.3
-
97
-
-
68949102678
-
-
Following the recent correspondence from Bolm and Buchwald (Angew Chem. Int. Ed, 2009, DOI: 10.1002/ anie.200902237) about the crucial role of copper (in commercial FeCl3) which can be responsible for a number of reactions alleged to be iron-catalyzed, we did, as an example, the reaction of 4-bromoacetophenone with phenylboronic acid in the presence of 10 mol% of FeCl3 (99.99% from Aldrich) in our standard conditions which led to a complete conversion and only to the product resulting from the cross-coupling reaction. Furthermore, when 1 mol% of Cu2O was added to FeCl3 99.99, even if the conversion was also complete, a mixture of products resulting of the cross-coupling (87, and from the homocoupling of boronic acid 13, was obtained. These reactions show clearly that iron is the catalyst for this Suzuki crosscoupling reaction
-
3 99.99%, even if the conversion was also complete, a mixture of products resulting of the cross-coupling (87%) and from the homocoupling of boronic acid (13%) was obtained. These reactions show clearly that iron is the catalyst for this Suzuki crosscoupling reaction.
-
-
-
|