-
1
-
-
0036589259
-
-
Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
-
(2002)
Chem. Rev.
, vol.102
, pp. 1359
-
-
Hassan, J.1
Sévignon, M.2
Gozzi, C.3
Schulz, E.4
Lemaire, M.5
-
2
-
-
72449170089
-
-
An excellent recent review: Ackermann, L.; Vincente, R.; Kapdi, A. R. Angew. Chem. Int. Ed. 2009, 48, 9792.
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 9792
-
-
Ackermann, L.1
Vincente, R.2
Kapdi, A.R.3
-
3
-
-
0000683502
-
-
Early important works in this field: (a) Nakamura, N.; Tajima, Y.; Sakai, K. Heterocycles 1982, 17, 235.
-
(1982)
Heterocycles
, vol.17
, pp. 235
-
-
Nakamura, N.1
Tajima, Y.2
Sakai, K.3
-
4
-
-
85009569241
-
-
(b) Akita, Y.; Itagaki, Y.; Takizawa, S.; Ohta, A. Chem Pharm. Bull. 1989, 37, 1477.
-
(1989)
Chem Pharm. Bull.
, vol.37
, pp. 1477
-
-
Akita, Y.1
Itagaki, Y.2
Takizawa, S.3
Ohta, A.4
-
5
-
-
0000882066
-
-
(c) Ohta, A.; Akita, Y.; Ohkuwa, T.; Chiba, M.; Fukunaga, R.; Miyafuji, A.; Nakata, T.; Tani, N.; Aoyagi, Y. Heterocycles 1990, 31, 1951.
-
(1990)
Heterocycles
, vol.31
, pp. 1951
-
-
Ohta, A.1
Akita, Y.2
Ohkuwa, T.3
Chiba, M.4
Fukunaga, R.5
Miyafuji, A.6
Nakata, T.7
Tani, N.8
Aoyagi, Y.9
-
6
-
-
0001568295
-
-
(d) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc Jpn. 1998, 71, 467.
-
(1998)
Bull. Chem. Soc Jpn.
, vol.71
, pp. 467
-
-
Pivsa-Art, S.1
Satoh, T.2
Kawamura, Y.3
Miura, M.4
Nomura, M.5
-
7
-
-
53949088904
-
-
Reviews on transition metal-catalyzed C-C bond formation via C-H bond cleavage: (a) Kakiuchi, E.; Kochi, T. Synthesis 2008, 3013.
-
(2008)
Synthesis
, vol.3013
-
-
Kakiuchi, E.1
Kochi, T.2
-
9
-
-
9644275232
-
-
(a) Itami, K.; Yamazaki, D.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 15396.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 15396
-
-
Itami, K.1
Yamazaki, D.2
Yoshida, J.3
-
11
-
-
0037094021
-
-
Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am Chem. Soc. 2002, 124, 5286.
-
(2002)
J. Am Chem. Soc.
, vol.124
, pp. 5286
-
-
Okazawa, T.1
Satoh, T.2
Miura, M.3
Nomura, M.4
-
13
-
-
33748515918
-
-
(a) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. J. Am. Chem. Soc. 2006, 128, 11748.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 11748
-
-
Yanagisawa, S.1
Sudo, T.2
Noyori, R.3
Itami, K.4
-
14
-
-
43849100263
-
-
(b) Yanagisawa, S.; Sudo, T.; Noyori, R.; Itami, K. Tetrahedron 2008, 64, 6073.
-
(2008)
Tetrahedron
, vol.64
, pp. 6073
-
-
Yanagisawa, S.1
Sudo, T.2
Noyori, R.3
Itami, K.4
-
17
-
-
0001230097
-
-
(b) Jolly, R. S.; Ludtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965.
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 4965
-
-
Jolly, R.S.1
Ludtke, G.2
Sheehan, D.3
Livinghouse, T.4
-
18
-
-
0000551283
-
-
(c) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 1843
-
-
Wender, P.A.1
Jenkins, T.E.2
Suzuki, S.3
-
19
-
-
0031708442
-
-
(d) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem. Int. Ed. 1998, 37, 2248.
-
(1998)
Angew. Chem. Int. Ed.
, vol.37
, pp. 2248
-
-
Murakami, M.1
Ubukata, M.2
Itami, K.3
Ito, Y.4
-
20
-
-
78650176180
-
-
Selected other examples of Rh-catalyzed C-H/C-X biaryl coupling
-
A review on Rh-catalyzed C-H bond arylation of arenes: (a) Bouffard, J.; Itami, K. Top. Curr. Chem. 2010, 292, 231. Selected other examples of Rh-catalyzed C-H/C-X biaryl coupling:
-
(2010)
Top. Curr. Chem.
, vol.292
, pp. 231
-
-
Bouffard, J.1
Itami, K.2
-
21
-
-
0347296197
-
-
(b) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem. Int. Ed. 2003, 42, 112.
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 112
-
-
Bedford, R.B.1
Coles, S.J.2
Hursthouse, M.B.3
Limmert, M.E.4
-
22
-
-
0242352421
-
-
(c) Oi, S.; Watanabe, S.; Fukita, S.; Inoue, Y. Tetrahedron Lett. 2003, 44, 8665.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 8665
-
-
Oi, S.1
Watanabe, S.2
Fukita, S.3
Inoue, Y.4
-
23
-
-
17144431294
-
-
(d) Wang, X.; Lane, B. S.; Sames, D. J. Am. Chem. Soc. 2005, 127, 4996.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4996
-
-
Wang, X.1
Lane, B.S.2
Sames, D.3
-
25
-
-
51649122191
-
-
(f) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
-
(2008)
Acc. Chem. Res.
, vol.41
, pp. 1013
-
-
Lewis, J.C.1
Bergman, R.G.2
Ellman, J.A.3
-
27
-
-
5044219636
-
-
A sole example using Ir catalysts for C-H bond arylation of arenes (benzene derivatives) with iodoarenes: Fujita, K.; Nonogawa, M.; Yamaguchi, R. Chem. Commun. 2004, 1926.
-
(2004)
Chem. Commun.
, vol.1926
-
-
Fujita, K.1
Nonogawa, M.2
Yamaguchi, R.3
-
28
-
-
70349915658
-
-
Join, B.; Yamamoto, T.; Itami, K. Angew. Chem. Int. Ed. 2009, 48, 3644.
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 3644
-
-
Join, B.1
Yamamoto, T.2
Itami, K.3
-
31
-
-
65249162972
-
-
Canivet, J.; Yamaguchi, J.; Ban, I.; Itami, K. Org. Lett. 2009, 11, 1733.
-
(2009)
Org. Lett.
, vol.11
, pp. 1733
-
-
Canivet, J.1
Yamaguchi, J.2
Ban, I.3
Itami, K.4
-
32
-
-
65249095692
-
-
Other Ni-catalyzed C-H/C-X biaryl coupling: (a) Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Org Lett. 2009, 11, 1737.
-
(2009)
Org Lett.
, vol.11
, pp. 1737
-
-
Hachiya, H.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
33
-
-
67149144482
-
-
(b) Kobayashi, O.; Uraguchi, D.; Yamakawa, T. Org. Lett. 2009, 11, 2679.
-
(2009)
Org. Lett.
, vol.11
, pp. 2679
-
-
Kobayashi, O.1
Uraguchi, D.2
Yamakawa, T.3
-
34
-
-
79551565067
-
-
2 ($610 for 2 g).
-
2 ($610 for 2 g).
-
-
-
-
36
-
-
28944437578
-
-
(b) Becker, M. A.; Schumacher, H. R. Jr.; Wortmann, R. L.; MacDonald, P. A.; Eustace, D.; Palo, W. A.; Streit, J.; Joseph-Ridge, N. New Engl. J. Med. 2005, 353, 2450.
-
(2005)
New Engl. J. Med.
, vol.353
, pp. 2450
-
-
Becker, M.A.1
Schumacher Jr., H.R.2
Wortmann, R.L.3
MacDonald, P.A.4
Eustace, D.5
Palo, W.A.6
Streit, J.7
Joseph-Ridge, N.8
-
37
-
-
0037449776
-
-
(c) Okamoto, K.; Eger, B. T.; Nishino, T.; Kondo, S.; Pai, E. E.; Nishino, T. J. Biol. Chem. 2003, 278, 1848.
-
(2003)
J. Biol. Chem.
, vol.278
, pp. 1848
-
-
Okamoto, K.1
Eger, B.T.2
Nishino, T.3
Kondo, S.4
Pai, E.E.5
Nishino, T.6
-
38
-
-
0034286415
-
-
(a) Mukhopadhyay, S.; Rothenberg, G.; Gitis, D.; Baidossi, M.; Ponde, D. E.; Sasson, Y. J. Chem. Soc., Perkin Trans. 2 2000, 1809.
-
(2000)
J. Chem. Soc., Perkin Trans.
, vol.2
, pp. 1809
-
-
Mukhopadhyay, S.1
Rothenberg, G.2
Gitis, D.3
Baidossi, M.4
Ponde, D.E.5
Sasson, Y.6
-
39
-
-
29844433863
-
-
(b) Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 18020
-
-
Campeau, L.-C.1
Rousseaux, S.2
Fagnou, K.3
-
41
-
-
47749125841
-
-
(d) Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 9254
-
-
Cho, S.H.1
Hwang, S.J.2
Chang, S.3
-
42
-
-
57349094283
-
-
(e) Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 14926
-
-
Berman, A.M.1
Lewis, J.C.2
Bergman, R.G.3
Ellman, J.A.4
-
43
-
-
69349094999
-
-
(f) Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 12070
-
-
Tobisu, M.1
Hyodo, I.2
Chatani, N.3
-
49
-
-
0043172126
-
-
(f) Minisci, F.; Vismara, E.; Fontana, F.; Morini, G.; Serravalle, M.; Giordano, C. J. Org. Chem. 1986, 51, 4411.
-
(1986)
J. Org. Chem.
, vol.51
, pp. 4411
-
-
Minisci, F.1
Vismara, E.2
Fontana, F.3
Morini, G.4
Serravalle, M.5
Giordano, C.6
-
50
-
-
0001178882
-
-
(g) Studer, A.; Bossait, M.; Vasella, T. Org Lett. 2000, 2, 985.
-
(2000)
Org Lett.
, vol.2
, pp. 985
-
-
Studer, A.1
Bossait, M.2
Vasella, T.3
-
51
-
-
0000161221
-
-
(h) Orito, K.; Uchiito, S.; Satoh, Y.; Tatsuzawa, T.; Harada, R.; Tokuda, M. Org. Lett. 2000, 2, 307.
-
(2000)
Org. Lett.
, vol.2
, pp. 307
-
-
Orito, K.1
Uchiito, S.2
Satoh, Y.3
Tatsuzawa, T.4
Harada, R.5
Tokuda, M.6
-
52
-
-
0344084101
-
-
(i) Harrowven, D. C.; Sutton, B. J.; Coulton, S. Org. Biomol. Chem. 2003, 1, 4047.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 4047
-
-
Harrowven, D.C.1
Sutton, B.J.2
Coulton, S.3
-
53
-
-
3042608169
-
-
(j) Núñez, A.; Sánchez, A.; Burgos, C.; Alvarez-Builla, J. Tetrahedron 2004, 60, 6217.
-
(2004)
Tetrahedron
, vol.60
, pp. 6217
-
-
Núñez, A.1
Sánchez, A.2
Burgos, C.3
Alvarez-Builla, J.4
-
55
-
-
58449085051
-
-
Yanagisawa, S.; Ueda, K.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 4673.
-
(2008)
Org. Lett.
, vol.10
, pp. 4673
-
-
Yanagisawa, S.1
Ueda, K.2
Taniguchi, T.3
Itami, K.4
-
56
-
-
14644427257
-
-
Although we hold the temperature at 50 °C, this is the bulk temperature of reaction mixture. As well documented, we assume that the reaction is taking place at high-temperature "hotspots" that are generated by microwave irradiation. For reviews on the use of microwave in organic synthesis, see: (a) de la Hoz, A.; Díaz-Oritiz, Á.; Moreno, A. Chem. Soc. Rev. 2005, 34, 164.
-
(2005)
Chem. Soc. Rev.
, vol.34
, pp. 164
-
-
De La Hoz, A.1
Díaz-Oritiz, Á.2
Moreno, A.3
-
58
-
-
11844268057
-
-
Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 161
-
-
Arvela, R.K.1
Leadbeater, N.E.2
Sangi, M.S.3
Williams, V.A.4
Granados, P.5
Singer, R.D.6
-
59
-
-
58449108832
-
-
Deng, G.; Ueda, K.; Yanagisawa, S.; Itami, K.; Li, C.-J. Chem. Eur. J. 2009, 15, 333.
-
(2009)
Chem. Eur. J.
, vol.15
, pp. 333
-
-
Deng, G.1
Ueda, K.2
Yanagisawa, S.3
Itami, K.4
Li, C.-J.5
-
60
-
-
54049087464
-
-
Ban, I.; Sudo, T.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 3607.
-
(2008)
Org. Lett.
, vol.10
, pp. 3607
-
-
Ban, I.1
Sudo, T.2
Taniguchi, T.3
Itami, K.4
-
61
-
-
34250029481
-
-
Selected recent examples:(a) Kuo, W.-J.; Chen, Y.-H.; Jeng, R.-J.; Chan, L.-H.; Lin, W.-P.; Yang, Z.-M. Tetrahedron 2007, 63, 7086.
-
(2007)
Tetrahedron
, vol.63
, pp. 7086
-
-
Kuo, W.-J.1
Chen, Y.-H.2
Jeng, R.-J.3
Chan, L.-H.4
Lin, W.-P.5
Yang, Z.-M.6
-
62
-
-
79551566136
-
-
Jpn. Kokai Tokkyo Koho JP2005232159
-
(b) Yabe, M.; Fugono, M. Jpn. Kokai Tokkyo Koho JP2005232159; Chem. Abstr. 143: 266809.
-
Chem. Abstr.
, vol.143
, pp. 266809
-
-
Yabe, M.1
Fugono, M.2
-
63
-
-
0344240163
-
-
Lehuédé, J.; Fauconneau, B.; Barrier, L.;Ourakow, M.; Piriou, A.; Vierfond, J.-M. Eur. J. Med Chem. 1999, 34, 991.
-
(1999)
Eur. J. Med Chem.
, vol.34
, pp. 991
-
-
Lehuédé, J.1
Fauconneau, B.2
Barrier, L.3
Ourakow, M.4
Piriou, A.5
Vierfond, J.-M.6
-
64
-
-
34249936878
-
-
Oxidative C-H/C-H biaryl coupling catalyzed by Pd and mediated by Cu or Ag: (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
-
(2007)
Science
, vol.316
, pp. 1172
-
-
Stuart, D.R.1
Fagnou, K.2
-
65
-
-
34547960227
-
-
(b) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. 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
-
68
-
-
35048815950
-
-
(e) Stuart, D. R.; Villemure, E.; Fagnou, K. 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
-
69
-
-
38849126856
-
-
(f) Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem. Int. Ed. 2008, 47, 1115.
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 1115
-
-
Li, B.-J.1
Tian, S.-L.2
Fang, Z.3
Shi, Z.-J.4
-
70
-
-
33947644069
-
-
Oxidative C-H/C-M biaryl coupling catalyzed by Pd and mediated by Cu or Ag: (a) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 3510
-
-
Giri, R.1
Maugel, N.2
Li, J.-J.3
Wang, D.-H.4
Breazzano, S.P.5
Saunders, L.B.6
Yu, J.-Q.7
-
71
-
-
34249056813
-
-
(b) Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 6066
-
-
Yang, S.1
Li, B.2
Wan, X.3
Shi, Z.4
-
72
-
-
34547212729
-
-
(c) Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem. Int. Ed. 2007, 46, 5554.
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 5554
-
-
Shi, Z.1
Li, B.2
Wan, X.3
Cheng, J.4
Fang, Z.5
Cao, B.6
Qin, C.7
Wang, Y.8
-
73
-
-
39849083252
-
-
(d) Yang, S.-D.; Sun, C.-L.; Fang, Z.; Li, B.-J.; Li, Y-Z.; Shi, Z.-J. Angew. Chem. Int. Ed. 2008, 47, 1473.
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 1473
-
-
Yang, S.-D.1
Sun, C.-L.2
Fang, Z.3
Li, B.-J.4
Li, Y.-Z.5
Shi, Z.-J.6
-
74
-
-
40549087300
-
-
(e) Kawai, H.; Kobayashi, Y.; Oi, S.; Inoue, Y. Chem. Commun. 2008, 1464.
-
(2008)
Chem. Commun.
, vol.1464
-
-
Kawai, H.1
Kobayashi, Y.2
Oi, S.3
Inoue, Y.4
-
75
-
-
70350054836
-
-
(a) Yanagisawa, S.; Ueda, K.; Sekizawa, H.; Itami, K. J. Am. Chem. Soc. 2009, 131, 14622.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 14622
-
-
Yanagisawa, S.1
Ueda, K.2
Sekizawa, H.3
Itami, K.4
-
77
-
-
55049131762
-
-
Nakano, M.; Tsurugi, H.; Satoh, T.; Miura, M. Org. Lett. 2008, 10, 1851.
-
(2008)
Org. Lett.
, vol.10
, pp. 1851
-
-
Nakano, M.1
Tsurugi, H.2
Satoh, T.3
Miura, M.4
-
78
-
-
77949455618
-
-
Roger, J.; Gottumukkala, A. L.; Doucet, H. ChemCatChem 2010, 2, 20.
-
(2010)
ChemCatChem
, vol.2
, pp. 20
-
-
Roger, J.1
Gottumukkala, A.L.2
Doucet, H.3
-
80
-
-
33846048526
-
-
(b) Sugie, A.; Kobayashi, K.; Suzaki, Y.; Osakada, K.; Mori, A. Chem. Lett. 2006, 35, 1100.
-
(2006)
Chem. Lett.
, vol.35
, pp. 1100
-
-
Sugie, A.1
Kobayashi, K.2
Suzaki, Y.3
Osakada, K.4
Mori, A.5
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