-
1
-
-
33947488258
-
-
For rare examples of stoichiometric and catalytic C-H activation by nickel, see: (a) Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544.
-
(1963)
J. Am. Chem. Soc.
, vol.85
, pp. 1544
-
-
Kleiman, J.P.1
Dubeck, M.2
-
2
-
-
33751553536
-
-
(b) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2554.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 2554
-
-
Tsuda, T.1
Kiyoi, T.2
Saegusa, T.3
-
3
-
-
1642291793
-
-
(c) Brunkan, N. M.; Brestensky, D. M.; Jones, W. D. J. Am. Chem. Soc. 2004, 126, 3627.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3627
-
-
Brunkan, N.M.1
Brestensky, D.M.2
Jones, W.D.3
-
4
-
-
2942545879
-
-
(d) Clement, N. D.; Cavell, K. J.; Jones, C.; Elsevier, C. J. Angew. Chem., Int. Ed. 2004, 43, 1277.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 1277
-
-
Clement, N.D.1
Cavell, K.J.2
Jones, C.3
Elsevier, C.J.4
-
5
-
-
4544294920
-
-
(e) Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 3845
-
-
Clement, N.D.1
Cavell, K.J.2
-
6
-
-
11144300921
-
-
(f) Ogoshi, S.; Ueta, M.; Oka, M.; Kurosawa, H. Chem. Commun. 2004, 2732.
-
(2004)
Chem. Commun.
, pp. 2732
-
-
Ogoshi, S.1
Ueta, M.2
Oka, M.3
Kurosawa, H.4
-
8
-
-
7444242751
-
-
For ligand-dependent divergent nickel catalysis on the reactions of benzonitrile with alkynes, see: (a) Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13904
-
-
Nakao, Y.1
Oda, S.2
Hiyama, T.3
-
10
-
-
33745657316
-
-
(c) McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. J. Am. Chem. Soc. 2004, 127, 13904.
-
(2004)
J. Am. Chem. Soc.
, vol.127
, pp. 13904
-
-
McCormick, M.M.1
Duong, H.A.2
Zuo, G.3
Louie, J.4
-
11
-
-
33745644106
-
-
note
-
A stereochemically unidentified product derived from the insertion of two molecules of 2a into the Ar-H bond at the C-2 position of 1b was also obtained in 31% yield.
-
-
-
-
12
-
-
33745646826
-
-
note
-
3 were found totally ineffective for the present hydroarylation.
-
-
-
-
13
-
-
33745647946
-
-
note
-
2 in the absence of an alkyne; see also ref 1f.
-
-
-
-
14
-
-
33745641972
-
-
note
-
1.
-
-
-
-
15
-
-
33745678583
-
-
note
-
1 and methyl 1-methylindole-3-carboxylate (1c) with 2a (1.0 mmol) under the identical conditions did not cause intermolecular deuterium crossover.
-
-
-
-
16
-
-
33745676168
-
-
note
-
3. (Diagram presented)
-
-
-
-
17
-
-
0034677867
-
-
For trans-selective hydroarylations of alkynes via electrophilic metalation, see: (a) 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
-
18
-
-
0037448880
-
-
(b) Trost, B. M.; Toste, F. D.; Greenman, K. J. Am. Chem. Soc. 2003, 125, 4518.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 4518
-
-
Trost, B.M.1
Toste, F.D.2
Greenman, K.3
-
20
-
-
33745642191
-
-
note
-
Similar regiochemistry was also reported for hydronickelation of unsymmetrical alkynes; see entries 16-18 of Table 2 and refs 1b and If.
-
-
-
-
21
-
-
0003112681
-
-
For representative examples of cis-hydroarylation of alkynes via oxidative addition of an Ar-H bond at high temperature or under irradiation, see: (a) Hong, P.; Cho, B.-R.; Yamazaki, H. Chem. Lett. 1979, 339.
-
(1979)
Chem. Lett.
, pp. 339
-
-
Hong, P.1
Cho, B.-R.2
Yamazaki, H.3
-
22
-
-
0024770215
-
-
(b) Tokunaga, Y.; Sakakura, T.; Tanaka, M. J. Mol. Catal. 1989, 56, 305.
-
(1989)
J. Mol. Catal.
, vol.56
, pp. 305
-
-
Tokunaga, Y.1
Sakakura, T.2
Tanaka, M.3
-
23
-
-
0000961051
-
-
(c) Aulwurm, U. R.; Melchinger, J. U.: Kisch, H. Organometallics 1995, 14, 3385.
-
(1995)
Organometallics
, vol.14
, pp. 3385
-
-
Aulwurm, U.R.1
Melchinger, J.U.2
Kisch, H.3
-
24
-
-
0002214869
-
-
(d) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681.
-
(1995)
Chem. Lett.
, pp. 681
-
-
Kakiuchi, F.1
Yamamoto, Y.2
Chatani, N.3
Murai, S.4
-
25
-
-
0033245490
-
-
(e) Satoh, T.; Nishinaka, Y.; Miura, M.; Nomura, M. Chem. Lett. 1999, 615.
-
(1999)
Chem. Lett.
, pp. 615
-
-
Satoh, T.1
Nishinaka, Y.2
Miura, M.3
Nomura, M.4
-
26
-
-
0035533839
-
-
(f) Kakiuchi, F.; Sato, T.; Igi, K.; Chatani, N.; Murai, S. Chem. Lett. 2001, 386.
-
(2001)
Chem. Lett.
, pp. 386
-
-
Kakiuchi, F.1
Sato, T.2
Igi, K.3
Chatani, N.4
Murai, S.5
-
27
-
-
0141855014
-
-
(g) Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J.-B.; Jun, C.-H. Org. Lett. 2003, 5, 2759.
-
(2003)
Org. Lett.
, vol.5
, pp. 2759
-
-
Lim, S.-G.1
Lee, J.H.2
Moon, C.W.3
Hong, J.-B.4
Jun, C.-H.5
-
28
-
-
30844466406
-
-
(h) Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 202
-
-
Kuninobu, Y.1
Tokunaga, Y.2
Kawata, A.3
Takai, K.4
-
29
-
-
0141989922
-
-
The mechanism of cis-hydroarylation of alkynes catalyzed by dinuclear palladium complexes is unclear. See: (i) Tsukada, N.; Mitsuboshi, T.; Setoguchi, H.; Inoue, Y. J. Am. Chem. Soc. 2003, 125, 12102.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 12102
-
-
Tsukada, N.1
Mitsuboshi, T.2
Setoguchi, H.3
Inoue, Y.4
-
31
-
-
0037077582
-
-
(b) García, J. J.; Brunkan, N. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 9547.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 9547
-
-
García, J.J.1
Brunkan, N.M.2
Jones, W.D.3
-
32
-
-
33745641758
-
-
note
-
At present, the following (hetero)arenes have failed to participate in the reaction: 4-(trifluoromethyl)benzonitrile, methyl 4-(trifluoromethyl)ben- zoatc, ethyl 1-methylindole-2-carboxylate, 1-methylpyrrole, 1-methyl imidazole. Unsubstituted indoles gave a mixture of 2- and 3-alkenylated products.
-
-
-
-
33
-
-
33745678127
-
-
note
-
3), catalyst at 115 °C has been reported to give the corresponding adduct as a mixture of stereoisomers in 42% yield; see ref 9f.
-
-
-
-
34
-
-
33745679026
-
-
note
-
Terminal alkynes failed to give the corresponding adducts due to rapid background oligomerization of alkynes.
-
-
-
-
37
-
-
0000171099
-
-
(c) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 493
-
-
Chatani, N.1
Fukuyama, T.2
Kakiuchi, F.3
Murai, S.4
-
38
-
-
0034699309
-
-
(d) Lu, W.; Jia, C.; Kitamura, T.; Fujiwara, Y. Org. Lett. 2000, 2, 2927.
-
(2000)
Org. Lett.
, vol.2
, pp. 2927
-
-
Lu, W.1
Jia, C.2
Kitamura, T.3
Fujiwara, Y.4
-
39
-
-
0037184456
-
-
(e) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 13964.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 13964
-
-
Tan, K.L.1
Bergman, R.G.2
Ellman, J.A.3
-
40
-
-
9144234212
-
-
(f) Pittard, K. A.; Lee, J. P.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. Organometallics 2004, 23, 5514.
-
(2004)
Organometallics
, vol.23
, pp. 5514
-
-
Pittard, K.A.1
Lee, J.P.2
Cundari, T.R.3
Gunnoe, T.B.4
Petersen, J.L.5
-
43
-
-
1342332903
-
-
(i) Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581.
-
(2004)
Org. Lett.
, vol.6
, pp. 581
-
-
Youn, S.W.1
Pastine, S.J.2
Sames, D.3
-
44
-
-
1642281558
-
-
(j) Liu, C.; Han, X.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 3700.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 3700
-
-
Liu, C.1
Han, X.2
Wang, X.3
Widenhoefer, R.A.4
-
45
-
-
5444275842
-
-
(k) Tan, K. L.; Park, S.; Ellman, J. A.; Bergman, R. G. J. Org. Chem. 2004, 69, 7329.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 7329
-
-
Tan, K.L.1
Park, S.2
Ellman, J.A.3
Bergman, R.G.4
-
46
-
-
18844405201
-
-
(l) Grimster, N. P.; Gauntlett, C.; Godfrey, C. R. A.; Gaunt, M. J. Angew. Chem., Int. Ed. 2005, 44, 3125.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 3125
-
-
Grimster, N.P.1
Gauntlett, C.2
Godfrey, C.R.A.3
Gaunt, M.J.4
-
47
-
-
26244458045
-
-
(m) Tsukada, N.; Murata, K.; Inoue, Y. Tetrahedron Lett. 2005, 46, 7515.
-
(2005)
Tetrahedron Lett.
, vol.46
, pp. 7515
-
-
Tsukada, N.1
Murata, K.2
Inoue, Y.3
-
48
-
-
0030848347
-
-
For hydroarylation of alkynes via the Friedel-Crafts alkenylations, see: (a) Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. 1997, 36, 1313.
-
(1997)
Angew. Chem., Int. Ed.
, vol.36
, pp. 1313
-
-
Yamaguchi, M.1
Kido, Y.2
Hayashi, A.3
Hirama, M.4
-
49
-
-
0034618620
-
-
(b) Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573.
-
(2000)
Chem. Commun.
, pp. 1573
-
-
Tsuchimoto, T.1
Maeda, T.2
Shirakawa, E.3
Kawakami, Y.4
-
52
-
-
0037872649
-
-
For selected recent work on intermolecular transition-metal-catalyzed C-C bond formation of indoles via C-H activation, see: (a) Sawada, T.; Fuerst, D. E.; Wood, J. L. Tetrahedron Lett. 2003, 44, 4919.
-
(2003)
Tetrahedron Lett.
, vol.44
, pp. 4919
-
-
Sawada, T.1
Fuerst, D.E.2
Wood, J.L.3
-
54
-
-
20444370318
-
-
(c) Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 8050
-
-
Lane, B.S.1
Brown, M.A.2
Sames, D.3
-
55
-
-
33646137411
-
-
(d) Deprez, N. R.; Kalyani, D.; Krause, A.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 4972
-
-
Deprez, N.R.1
Kalyani, D.2
Krause, A.3
Sanford, M.S.4
-
56
-
-
33745646825
-
-
For selected recent work on intermolecular transition-metal-catalyzed C-C bond formation of other heteroarenes via C-H activation, see: (a) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 4667.
-
(1998)
Bull. Chem. Soc. Jpn.
, vol.71
, pp. 4667
-
-
Pivsa-Art, S.1
Satoh, T.2
Kawamura, Y.3
Miura, M.4
Nomura, M.5
-
57
-
-
0037442583
-
-
(b) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1700
-
-
Mori, A.1
Sekiguchi, A.2
Masui, K.3
Shimada, T.4
Horie, M.5
Osakada, K.6
Kawamoto, M.7
Ikeda, T.8
-
59
-
-
1542345322
-
-
(d) Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 2300
-
-
Dick, A.R.1
Hull, K.L.2
Sanford, M.S.3
-
60
-
-
18744369931
-
-
(e) Bellina, F.; Cauteruccio, S.; Mannina, L.; Rossi, R.; Viel, S. J. Org. Chem. 2005, 70, 3997.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 3997
-
-
Bellina, F.1
Cauteruccio, S.2
Mannina, L.3
Rossi, R.4
Viel, S.5
-
61
-
-
29844433863
-
-
(f) 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
-
62
-
-
31544455027
-
-
(g) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 581
-
-
Campeau, L.-C.1
Parisien, M.2
Jean, A.3
Fagnou, K.4
-
63
-
-
33745656245
-
-
(h) Lewis, J. C.; Wu, J. Y.; Bergman, R. G.; Ellman, J. A. Angew. Chem., Int. Ed. 2006, 45, 1589.
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 1589
-
-
Lewis, J.C.1
Wu, J.Y.2
Bergman, R.G.3
Ellman, J.A.4
|