-
3
-
-
77949381429
-
-
Recent reviews on C-H functionalization using transition metals: Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
-
(2010)
Chem. Rev.
, vol.110
, pp. 1147
-
-
Lyons, T.W.1
Sanford, M.S.2
-
4
-
-
77349090183
-
-
Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
-
(2010)
Chem. Rev.
, vol.110
, pp. 624
-
-
Colby, D.A.1
Bergman, R.G.2
Ellman, J.A.3
-
5
-
-
75749111062
-
-
Xu, L.-M.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712
-
(2010)
Chem. Soc. Rev.
, vol.39
, pp. 712
-
-
Xu, L.-M.1
Yang, Z.2
Shi, Z.-J.3
-
6
-
-
72449170089
-
-
Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 9792
-
-
Ackermann, L.1
Vicente, R.2
Kapdi, A.R.3
-
7
-
-
67649488045
-
-
Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 5094
-
-
Chen, X.1
Engle, K.M.2
Wang, D.-H.3
Yu, J.-Q.4
-
8
-
-
70350494926
-
-
Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
-
(2009)
Chem. Soc. Rev.
, vol.38
, pp. 3242
-
-
Giri, R.1
Shi, B.-F.2
Engle, K.M.3
Maugel, N.4
Yu, J.-Q.5
-
12
-
-
33846918696
-
-
Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
-
(2007)
Chem. Rev.
, vol.107
, pp. 174
-
-
Alberico, D.1
Scott, M.E.2
Lautens, M.3
-
13
-
-
74549178746
-
-
Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
-
(2010)
Chem. Commun.
, vol.46
, pp. 677
-
-
Sun, C.-L.1
Li, B.-J.2
Shi, Z.-J.3
-
14
-
-
0002591690
-
-
Reviews:; Acc. Chem. Res. 2001, 34, 633
-
First report: Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119 Reviews: Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
-
(1967)
Tetrahedron Lett.
, vol.8
, pp. 1119
-
-
Moritani, I.1
Fujiwara, Y.2
Jia, C.3
Kitamura, T.4
Fujiwara, Y.5
-
15
-
-
36849030278
-
-
Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. 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
-
16
-
-
0037181051
-
-
Selected Pd-catalyzed oxidative olefinations: Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. 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
-
18
-
-
34250861444
-
-
Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 7666
-
-
Cai, G.1
Fu, Y.2
Li, Y.3
Wan, X.4
Shi, Z.5
-
19
-
-
52049102506
-
-
Li, J.-J.; Mei, T.-S.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 6452
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 6452
-
-
Li, J.-J.1
Mei, T.-S.2
Yu, J.-Q.3
-
20
-
-
53249142637
-
-
Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 7230
-
-
Würtz, S.1
Rakshit, S.2
Neumann, J.J.3
Dröge, T.4
Glorius, F.5
-
21
-
-
70349928947
-
-
García-Rubia, A.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 6511
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 6511
-
-
García-Rubia, A.1
Arrayás, R.G.2
Carretero, J.C.3
-
22
-
-
67749142079
-
-
Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 5072
-
-
Zhang, Y.-H.1
Shi, B.-F.2
Yu, J.-Q.3
-
23
-
-
74549148904
-
-
Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315
-
(2010)
Science
, vol.327
, pp. 315
-
-
Wang, D.-H.1
Engle, K.M.2
Shi, B.-F.3
Yu, J.-Q.4
-
25
-
-
77952578429
-
-
Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 5916
-
-
Lu, Y.1
Wang, D.-H.2
Engle, K.M.3
Yu, J.-Q.4
-
26
-
-
48749120080
-
-
Mild oxidative Heck reaction for activated diene olefins, see: Houlden, C. E.; Bailey, C. D.; Ford, J. G.; Gagné, M. R.; Lloyd-Jones, G. C.; Booker-Milburn, K. I. J. Am. Chem. Soc. 2008, 130, 10066
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 10066
-
-
Houlden, C.E.1
Bailey, C.D.2
Ford, J.G.3
Gagné, M.R.4
Lloyd-Jones, G.C.5
Booker-Milburn, K.I.6
-
27
-
-
0035900977
-
-
Ru-catalyzed: Weissman, H.; Song, X.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 337
-
-
Weissman, H.1
Song, X.2
Milstein, D.3
-
28
-
-
34147156671
-
-
Rh-catalyzed: Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407
-
(2007)
Org. Lett.
, vol.9
, pp. 1407
-
-
Ueura, K.1
Satoh, T.2
Miura, M.3
-
29
-
-
34447327520
-
-
Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362
-
(2007)
J. Org. Chem.
, vol.72
, pp. 5362
-
-
Ueura, K.1
Satoh, T.2
Miura, M.3
-
30
-
-
70249093328
-
-
Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094
-
(2009)
J. Org. Chem.
, vol.74
, pp. 7094
-
-
Umeda, N.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
31
-
-
77951788947
-
-
Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2068
-
(2010)
Org. Lett.
, vol.12
, pp. 2068
-
-
Morimoto, K.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
33
-
-
77954637248
-
-
Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 9585
-
-
Rakshit, S.1
Patureau, F.W.2
Glorius, F.3
-
35
-
-
78650375862
-
-
See also: Wang, F.; Song, G.; Li, X. Org. Lett. 2010, 12, 5430
-
(2010)
Org. Lett.
, vol.12
, pp. 5430
-
-
Wang, F.1
Song, G.2
Li, X.3
-
36
-
-
79951864896
-
-
101002/anie201007241
-
For a recent minireview, see: Patureau, F.; Glorius, F. Angew. Chem., Int. Ed. 2011, 10.1002/anie.201007241 It is interesting to note that, whereas the term "external oxidant" seems to be unambiguous, the term "internal oxidant" can either mean simply that one of the substrates acts as an oxidation equivalent or, in a more limited usage, that the catalyst gets oxidized internally before, at, or after the reaction event. For example, the halide group of aryl halides represents a truly internal oxidant in reactions like the Heck reaction.
-
(2011)
Angew. Chem., Int. Ed.
-
-
Patureau, F.1
Glorius, F.2
-
37
-
-
70349617692
-
-
Wu, J.; Cui, X.; Chen, L.; Jiang, G.; Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 13888
-
-
Wu, J.1
Cui, X.2
Chen, L.3
Jiang, G.4
Wu, Y.5
-
39
-
-
77956620860
-
-
Ng, K.-H.; Chan, A. S. C.; Yu, W.-Y. J. Am. Chem. Soc. 2010, 132, 12862
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 12862
-
-
Ng, K.-H.1
Chan, A.S.C.2
Yu, W.-Y.3
-
40
-
-
77952570693
-
-
Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908. For the pioneering use of O -methyl hydroxamic acids (CONH(OMe)) as DG in C-H activation chemistry, see
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 6908
-
-
Guimond, N.1
Gouliaras, C.2
Fagnou, K.3
-
41
-
-
44949242600
-
-
Wang, D.-H; Wasa, M.; Giri, R; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 7190
-
-
Wang, D.-H.1
Wasa, M.2
Giri, R.3
Yu, J.-Q.4
-
43
-
-
79952266875
-
-
Interestingly, using N -hydroxybenzamide as substrate, 72% of product 3aa was obtained.
-
Interestingly, using N -hydroxybenzamide as substrate, 72% of product 3aa was obtained.
-
-
-
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44
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79952268947
-
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See Supporting Information for further details.
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See Supporting Information for further details.
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-
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45
-
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79952263596
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No dehalogenation or demethoxylation was observed.
-
No dehalogenation or demethoxylation was observed.
-
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-
-
46
-
-
79952272985
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1H NMR).
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1H NMR).
-
-
-
-
47
-
-
77949801096
-
-
In Pd(II)-catalyzed oxidative Heck reactions, the amide group is known for this kind of attack: Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680 Indeed, under our standard reaction conditions, we have also observed the five-membered lactam side product.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 3680
-
-
Wasa, M.1
Engle, K.M.2
Yu, J.-Q.3
-
48
-
-
43449134102
-
-
For recent direct catalytic C-H oxidative Heck couplings to ethylene, see: Kormos, C. M.; Leadbeater, N. E. J. Org. Chem. 2008, 73, 3854
-
(2008)
J. Org. Chem.
, vol.73
, pp. 3854
-
-
Kormos, C.M.1
Leadbeater, N.E.2
-
49
-
-
41549165729
-
-
Yamada, T.; Sakakura, A.; Sakaguchi, S.; Obora, Y.; Ishii, Y. New J. Chem. 2008, 32, 738
-
(2008)
New J. Chem.
, vol.32
, pp. 738
-
-
Yamada, T.1
Sakakura, A.2
Sakaguchi, S.3
Obora, Y.4
Ishii, Y.5
-
51
-
-
78049513726
-
-
Song, G.; Chen, D.; Pan, C.-L.; Crabtree, R. H.; Li, X. J. Org. Chem. 2010, 75, 7487
-
(2010)
J. Org. Chem.
, vol.75
, pp. 7487
-
-
Song, G.1
Chen, D.2
Pan, C.-L.3
Crabtree, R.H.4
Li, X.5
-
52
-
-
0001441077
-
-
Pd(II)-catalyzed Heck reaction: Ryabov, A. D.; Sakodinskaya, I. K.; Yatsimirsky, A. K. J. Organomet. Chem. 1991, 406, 309
-
(1991)
J. Organomet. Chem.
, vol.406
, pp. 309
-
-
Ryabov, A.D.1
Sakodinskaya, I.K.2
Yatsimirsky, A.K.3
-
53
-
-
78249254758
-
-
Rh(I) can bind effectively with olefin ligands: Hahn, B. T.; Tewes, F.; Fröhlich, R.; Glorius, F. Angew. Chem., Int. Ed. 2010, 122, 1161
-
(2010)
Angew. Chem., Int. Ed.
, vol.122
, pp. 1161
-
-
Hahn, B.T.1
Tewes, F.2
Fröhlich, R.3
Glorius, F.4
-
54
-
-
79952272626
-
-
V species could be invoked.
-
V species could be invoked.
-
-
-
-
56
-
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79952268948
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-
1H NMR or GC-MS of the crude reaction mixture. See Supporting Information for further details.
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1H NMR or GC-MS of the crude reaction mixture. See Supporting Information for further details.
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