-
1
-
-
4644349037
-
-
For lead references on Heck couplings, see: a, In, de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York
-
For lead references on Heck couplings, see: (a) Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: New York, 2004; p 217.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
, pp. 217
-
-
Bräse, S.1
De Meijere, A.2
-
2
-
-
22744442306
-
-
(b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 4442
-
-
Nicolaou, K.C.1
Bulger, P.G.2
Sarlah, D.3
-
4
-
-
0034677867
-
-
(b) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
-
(2000)
Science
, vol.287
, pp. 1992
-
-
Jia, C.1
Piao, D.2
Oyamada, J.3
Lu, W.4
Kitamura, T.5
Fujiwara, Y.6
-
5
-
-
0034867872
-
-
(c) Jia, C.; Kitamura, T.; Fujiwara, Y Acc. Chem. Res. 2001, 34, 633.
-
(2001)
Acc. Chem. Res.
, vol.34
, pp. 633
-
-
Jia, C.1
Kitamura, T.2
Fujiwara, Y.3
-
6
-
-
0037048663
-
-
For use of oxidative C-H olefination reactions in natural product synthesis, see: a
-
For use of oxidative C-H olefination reactions in natural product synthesis, see: (a) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 11856
-
-
Dangel, B.D.1
Godula, K.2
Youn, S.W.3
Sezen, B.4
Sames, D.5
-
7
-
-
43949108554
-
-
(b) Tsai, A. S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6316.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 6316
-
-
Tsai, A.S.1
Bergman, R.G.2
Ellman, J.A.3
-
8
-
-
52049102506
-
-
(a) 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
-
9
-
-
67749142079
-
-
(b) 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
-
10
-
-
74549148904
-
-
(c) 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
-
11
-
-
74949127669
-
-
(d) Shi, B.-F.; Zhang, Y.-H.; Lam, J. K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 460
-
-
Shi, B.-F.1
Zhang, Y.-H.2
Lam, J.K.3
Wang, D.-H.4
Yu, J.-Q.5
-
12
-
-
77949801096
-
-
(e) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3680.
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 3680
-
-
Wasa, M.1
Engle, K.M.2
Yu, J.-Q.3
-
13
-
-
0042531833
-
-
For intermolecular oxidative Heck couplings, see: a
-
For intermolecular oxidative Heck couplings, see: (a) Dams, M.; De Vos, D. E.; Celen, S.; Jacobs, P. A. Angew. Chem., Int. Ed. 2003, 42, 3512.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 3512
-
-
Dams, M.1
De Vos, D.E.2
Celen, S.3
Jacobs, P.A.4
-
14
-
-
0037433243
-
-
(b) Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1476
-
-
Yokota, T.1
Tani, M.2
Sakaguchi, S.3
Ishii, Y.4
-
15
-
-
18844405201
-
-
(c) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.
-
(2005)
J. Angew. Chem., Int. Ed.
, vol.44
, pp. 3125
-
-
Grimster, N.P.1
Gauntlett, C.2
Godfrey, C.R.A.3
Gaunt, M.4
-
16
-
-
34250861444
-
-
(d) 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
-
17
-
-
47749125841
-
-
(e) 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
-
18
-
-
70349928947
-
-
For intramolecular oxidative Heck couplings, see
-
(f) García-Rubia, A.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 6511. For intramolecular oxidative Heck couplings, see:
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 6511
-
-
García-Rubia, A.1
Arrayás, R.G.2
Carretero, J.C.3
-
20
-
-
10044267678
-
-
(h) Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 6144.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 6144
-
-
Zhang, H.1
Ferreira, E.M.2
Stoltz, B.M.3
-
21
-
-
53249142637
-
-
(i) 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
-
22
-
-
0037181051
-
-
See also
-
(a) 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. See also:
-
(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
-
23
-
-
34347323946
-
-
(b) Wang, J.-R.; Yang, C.-T.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 5449.
-
(2007)
Tetrahedron. Lett.
, vol.48
, pp. 5449
-
-
Wang, J.-R.1
Yang, C.-T.2
Liu, L.3
Guo, Q.-X.4
-
24
-
-
70249093328
-
-
See also
-
(a) Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7094. See also:
-
(2009)
J. Org. Chem.
, vol.74
, pp. 7094
-
-
Umeda, N.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
25
-
-
0000037010
-
-
(b) Miura, M.; Tsuda, T.; Satoh, T.; Pivsa-Art, S.; Nomura, M. J. Org. Chem. 1998, 63, 5211.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 5211
-
-
Miura, M.1
Tsuda, T.2
Satoh, T.3
Pivsa-Art, S.4
Nomura, M.5
-
26
-
-
34147156671
-
-
(c) 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
-
27
-
-
34447327520
-
-
(d) 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
-
28
-
-
77951788947
-
-
(e) 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
-
29
-
-
57549086217
-
-
Examples of C-H activations utilizing acetanilides as substrates: a
-
Examples of C-H activations utilizing acetanilides as substrates: (a) Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 16474
-
-
Stuart, D.R.1
Bertrand-Laperle, M.2
Burgess, K.M.N.3
Fagnou, K.4
-
33
-
-
33745043243
-
-
(e) Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 7416
-
-
Wan, X.1
Ma, Z.2
Li, B.3
Zhang, K.4
Cao, S.5
Zhang, S.6
Shi, Z.7
-
34
-
-
34547212729
-
-
(f) 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
-
35
-
-
34249056813
-
-
(g) 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
-
36
-
-
34248361209
-
-
(h) Campeau, L.-C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
-
(2007)
Aldrichimica Acta
, vol.40
, pp. 35
-
-
Campeau, L.-C.1
Stuart, D.R.2
Fagnou, K.3
-
37
-
-
77955791662
-
-
See Supporting Information for further information
-
See Supporting Information for further information.
-
-
-
-
38
-
-
84855627320
-
-
1H NMR of the crude products
-
1H NMR of the crude products.
-
-
-
-
39
-
-
77955837050
-
-
Steric congestion near the acetanilide directing group slows down the reaction and deteriorates the yield
-
Steric congestion near the acetanilide directing group slows down the reaction and deteriorates the yield:
-
-
-
-
40
-
-
77955779338
-
-
Increasing the temperature or the catalytic loading did not significantly improve the yield in this case. However, no side products were observed
-
Increasing the temperature or the catalytic loading did not significantly improve the yield in this case. However, no side products were observed.
-
-
-
-
41
-
-
76249084575
-
-
For the application of a structurally related olefin-oxazoline ligand in Rh catalysis, see
-
For the application of a structurally related olefin-oxazoline ligand in Rh catalysis, see: Hahn, B. T.; Tewes, F.; Frohlich, R.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 1143.
-
(2010)
Angew. Chem., Int. Ed.
, vol.49
, pp. 1143
-
-
Hahn, B.T.1
Tewes, F.2
Frohlich, R.3
Glorius, F.4
-
42
-
-
77955834162
-
-
high value of the TOF for the acrylate substrate is in accordance with previous reports on related transformations; see refs 2 and 3
-
The high value of the TOF for the acrylate substrate is in accordance with previous reports on related transformations; see refs 2 and 3.
-
-
-
-
43
-
-
77955831061
-
-
It should be noted that when 1-octene was engaged as a substrate, only trace amounts of product could be detected
-
It should be noted that when 1-octene was engaged as a substrate, only trace amounts of product could be detected.
-
-
-
-
44
-
-
65349176463
-
-
For styrene preparation through prior activation, see: a
-
For styrene preparation through prior activation, see: (a) Lindh, J.; Savmarker, J.; Nilsson, P.; Sjoberg, P. J. R.; Larhed, M. Chem.-Eur. J. 2009, 15, 4630.
-
(2009)
Chem.-Eur. J.
, vol.15
, pp. 4630
-
-
Lindh, J.1
Savmarker, J.2
Nilsson, P.3
Sjoberg, P.J.R.4
Larhed, M.5
-
45
-
-
73149124729
-
-
For direct catalytic C-H oxidative Heck coupling to ethylene, see
-
(b) Smith, C. R.; RajanBabu, T. V. Tetrahedron 2010, 66, 1102. For direct catalytic C-H oxidative Heck coupling to ethylene, see:
-
(2010)
Tetrahedron.
, vol.66
, pp. 1102
-
-
Smith, C.R.1
RajanBabu, T.V.2
-
46
-
-
0000875742
-
-
(c) Fujiwara, Y.; Moritani, I.; Danno, S.; Asano, R.; Teranishi, S. J. Am. Chem. Soc. 1969, 91, 7166.
-
(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 7166
-
-
Fujiwara, Y.1
Moritani, I.2
Danno, S.3
Asano, R.4
Teranishi, S.5
-
48
-
-
41549165729
-
-
For the vinylation of preformed palladacycles, see
-
(e) Yamada, T.; Sakakura, A.; Sakaguchi, S.; Obora, Y.; Ishii, Y. New J. Chem. 2008, 32, 738. For the vinylation of preformed palladacycles, see:
-
(2008)
New J. Chem.
, vol.32
, pp. 738
-
-
Yamada, T.1
Sakakura, A.2
Sakaguchi, S.3
Obora, Y.4
Ishii, Y.5
-
50
-
-
0344006321
-
-
For two of the many types of transformations of terminal olefins, see reviews on Ru catalyzed olefin metathesis: a
-
For two of the many types of transformations of terminal olefins, see reviews on Ru catalyzed olefin metathesis: (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
-
(2000)
Angew. Chem., Int. Ed.
, vol.39
, pp. 3012
-
-
Fürstner, A.1
-
51
-
-
3343012187
-
-
For an overview on Rh catalyzed hydroformylation, see
-
(b) Grubbs, R. H. Tetrahedron 2004, 60, 7117. For an overview on Rh catalyzed hydroformylation, see:
-
(2004)
Tetrahedron.
, vol.60
, pp. 7117
-
-
Grubbs, R.H.1
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