-
4
-
-
0036589261
-
-
(d) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
-
(2002)
Chem. Rev.
, vol.102
, pp. 1731
-
-
Ritleng, V.1
Sirlin, C.2
Pfeffer, M.3
-
5
-
-
30844431861
-
-
(a) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murni, S. J. Org. Chem. 1997, 62, 2004.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2004
-
-
Chatani, N.1
Ie, Y.2
Kakiuchi, F.3
Murni, S.4
-
6
-
-
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
-
7
-
-
11444263216
-
-
(c) Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687.
-
(2004)
Org. Lett.
, vol.6
, pp. 4687
-
-
Lim, S.-G.1
Ahn, J.-A.2
Jun, C.-H.3
-
8
-
-
0034827123
-
-
(a) Tan, K. L.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 2685.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 2685
-
-
Tan, K.L.1
Bergman, R.G.2
Ellman, J.A.3
-
9
-
-
0035802362
-
-
(b) Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9692
-
-
Thalji, R.K.1
Ahrendt, K.A.2
Bergman, R.G.3
Ellman, J.A.4
-
10
-
-
0141630581
-
-
(c) Tan, K. L.; Vasudevan, A.; Bergman, R. G.; Ellman, J. A.; Souers, A. J. Org. Lett. 2003, 5, 2131.
-
(2003)
Org. Lett.
, vol.5
, pp. 2131
-
-
Tan, K.L.1
Vasudevan, A.2
Bergman, R.G.3
Ellman, J.A.4
Souers, A.J.5
-
11
-
-
2942528733
-
-
(d) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7191.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 7191
-
-
Thalji, R.K.1
Ellman, J.A.2
Bergman, R.G.3
-
13
-
-
0001476026
-
-
For the synthesis of indene derivatives using transition metal compounds, see: (a) Liebeskind, L. S.; Gasdaska, J. R.; McCallum, J. S. J. Org. Chem. 1989, 54, 669.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 669
-
-
Liebeskind, L.S.1
Gasdaska, J.R.2
McCallum, J.S.3
-
14
-
-
0027965155
-
-
(b) Semmelhack, M. F.; Ho, S.; Cohen, D.; ,Steigerwald, M.; Lee, M. C.; Lee, G.; Gilbert, A. M.; Wulff, W. D.; Ball, R. G. J. Am. Chem. Soc. 1994, 116, 7108.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 7108
-
-
Semmelhack, M.F.1
Ho, S.2
Cohen, D.3
Steigerwald, M.4
Lee, M.C.5
Lee, G.6
Gilbert, A.M.7
Wulff, W.D.8
Ball, R.G.9
-
16
-
-
0033525480
-
-
(d) Romines, K. R.; Lovasz, K. D.; Mizsak, S. A.; Morris, J. K.; Seest, E. P.; Han, F.; Tulinsky, J.; Judge, T. M.; Gammill, R. B. J. Org. Chem. 1999, 64, 1733.
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1733
-
-
Romines, K.R.1
Lovasz, K.D.2
Mizsak, S.A.3
Morris, J.K.4
Seest, E.P.5
Han, F.6
Tulinsky, J.7
Judge, T.M.8
Gammill, R.B.9
-
17
-
-
0037458784
-
-
(e) Xi, Z.; Guo, R.; Mito, S.; Yan, H.; Kanno, K.-i.; Nakajima, K.; Takahashi, T. J. Org. Chem. 2003, 68, 1252.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 1252
-
-
Xi, Z.1
Guo, R.2
Mito, S.3
Yan, H.4
Kanno, K.-I.5
Nakajima, K.6
Takahashi, T.7
-
18
-
-
6344263860
-
-
(f) Ming-Yuan, L.; Madhushaw, R. J.; Liu, R.-S. J. Org. Chem. 2004, 69, 7700.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 7700
-
-
Ming-Yuan, L.1
Madhushaw, R.J.2
Liu, R.-S.3
-
19
-
-
3042740959
-
-
(g) Chang, K.-J.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004, 69, 4781.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 4781
-
-
Chang, K.-J.1
Rayabarapu, D.K.2
Cheng, C.-H.3
-
22
-
-
0033571369
-
-
3)-H bond activation has been reported: Chen, H.; Hartwig, J. F. Angew. Chem., Int. Ed Engl. 1999, 38, 3391.
-
(1999)
Angew. Chem., Int. Ed Engl.
, vol.38
, pp. 3391
-
-
Chen, H.1
Hartwig, J.F.2
-
23
-
-
0025465048
-
-
For the building blocks for functional materials, see: (a) Akbalut, U.; Khurshid, A.; Hacioglu, B.; Toppare, L. Polymer 1990, 31, 1343.
-
(1990)
Polymer
, vol.31
, pp. 1343
-
-
Akbalut, U.1
Khurshid, A.2
Hacioglu, B.3
Toppare, L.4
-
24
-
-
0032536393
-
-
(b) Barbera, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem., Int. Ed. Engl. 1998, 37, 296.
-
(1998)
Angew. Chem., Int. Ed. Engl.
, vol.37
, pp. 296
-
-
Barbera, J.1
Rakitin, O.A.2
Ros, M.B.3
Torroba, T.4
-
25
-
-
0034613160
-
-
(c) Yang, J.; Lakshnukantham, M. V.; Cava, M. P. J. Org. Chem. 2000, 65, 6739.
-
(2000)
J. Org. Chem.
, vol.65
, pp. 6739
-
-
Yang, J.1
Lakshnukantham, M.V.2
Cava, M.P.3
-
26
-
-
8644263966
-
-
and references therein
-
For the building blocks for medicines, see: Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 13, 2397 and references therein.
-
(2004)
Synlett
, vol.13
, pp. 2397
-
-
Korte, A.1
Legros, J.2
Bolm, C.3
-
28
-
-
0033303413
-
-
For the use as ligands for transition metals by deprotonation, see: (a) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-195, 147.
-
(1999)
Coord. Chem. Rev.
, vol.193-195
, pp. 147
-
-
Cadierno, V.1
Diez, J.2
Gamasa, M.P.3
Gimeno, J.4
Lastra, E.5
-
31
-
-
0002043236
-
-
Phthalimidine (isoindolinone, benzo-γ-lactam) has a five-membered ring with one nitrogen atom and is a part of the structure of bioactive compounds: (a) Fajardo, V.; Elango, V.; Cassels, B. K.; Shamma, M. Tetrahedron Lett. 1982, 23, 39.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 39
-
-
Fajardo, V.1
Elango, V.2
Cassels, B.K.3
Shamma, M.4
-
32
-
-
0001559304
-
-
(b) Valencia, E.; Freyer, A. J.; Shamma, M. Tetrahedron Lett. 1984, 25, 599.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 599
-
-
Valencia, E.1
Freyer, A.J.2
Shamma, M.3
-
33
-
-
0000950433
-
-
(c) Valencia, E.; Fajardo, V.; Freyer, A. J.; Shamma, M. Tetrahedron Lett. 1985, 26, 993.
-
(1985)
Tetrahedron Lett.
, vol.26
, pp. 993
-
-
Valencia, E.1
Fajardo, V.2
Freyer, A.J.3
Shamma, M.4
-
34
-
-
0000492940
-
-
and references therein
-
(d) Takahashi, I.; Kawakami, T.; Hirano, E.; Yokota, H.; Kitajimu, H. Synlett 1996, 353 and references therein.
-
(1996)
Synlett
, pp. 353
-
-
Takahashi, I.1
Kawakami, T.2
Hirano, E.3
Yokota, H.4
Kitajimu, H.5
-
35
-
-
3042825440
-
-
(e) Moreau, A.; Couture, A.; Deniau, E.; Grandelaudon, P. J. Org. Chem. 2004, 69, 4527.
-
(2004)
J. Org. Chem.
, vol.69
, pp. 4527
-
-
Moreau, A.1
Couture, A.2
Deniau, E.3
Grandelaudon, P.4
-
36
-
-
0001477080
-
-
Several synthetic methods of phthalimidine derivatives using transition metal compounds have been reported: (a) Uozumi, Y.; Kawasaki, N.; Mori, E.; Mori, M.; Shibasaki, M. J. Am. Chem. Soc. 1989, 111, 3725.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 3725
-
-
Uozumi, Y.1
Kawasaki, N.2
Mori, E.3
Mori, M.4
Shibasaki, M.5
-
37
-
-
1542397422
-
-
(b) Duckworth, D. M.; Lee-Wong, S.; Slawin, A. M. Z.; Smith, E. H.; Williams, D. J. J. Chem. Soc., Perkin Trans. 1 1996, 815.
-
(1996)
J. Chem. Soc., Perkin Trans. 1
, pp. 815
-
-
Duckworth, D.M.1
Lee-Wong, S.2
Slawin, A.M.Z.3
Smith, E.H.4
Williams, D.J.5
-
38
-
-
4043137475
-
-
(c) Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
-
(2004)
Org. Lett.
, vol.6
, pp. 2511
-
-
Couty, S.1
Liegault, B.2
Meyer, C.3
Cossy, J.4
-
39
-
-
7744224233
-
-
Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 14342
-
-
Orito, K.1
Horibata, A.2
Nakamura, T.3
Ushito, H.4
Nagasaki, H.5
Yuguchi, M.6
Yamashita, S.7
Tokuda, M.8
-
40
-
-
30844443383
-
-
note
-
1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
-
-
-
-
41
-
-
30844459812
-
-
note
-
Heat and/or a rhenium catalyst promote interconversion of substituents at 1,2-position of the indene framework. The elucidation of the mechanism is now under consideration.
-
-
-
-
42
-
-
0032257316
-
-
Kakiuchi, F.; Sato, T.; Tsujimoto, T.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1998, 1053.
-
(1998)
Chem. Lett.
, pp. 1053
-
-
Kakiuchi, F.1
Sato, T.2
Tsujimoto, T.3
Yamauchi, M.4
Chatani, N.5
Murai, S.6
-
43
-
-
6044253710
-
-
There is another possible pathway: C-H bond activation is reversible and can occur at all positions on the aromatic ring. After C-H bond activation, the coordinating group acts to trap the ortho-C-H bond addition product and stable chelated intermediate. See: Zhang, X.; Kanzelberger, M.; Emge, T. J.; Goldman, A. S. J. Am. Chem. Soc. 2004, 126, 13192.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 13192
-
-
Zhang, X.1
Kanzelberger, M.2
Emge, T.J.3
Goldman, A.S.4
-
44
-
-
0038276580
-
-
5: (a) Böhm, A.; Sünkel, K.; Polborn, K.; Beck, W. J. Organomet. Chem. 1998, 552, 237.
-
(1998)
J. Organomet. Chem.
, vol.552
, pp. 237
-
-
Böhm, A.1
Sünkel, K.2
Polborn, K.3
Beck, W.4
-
45
-
-
0000444290
-
-
5: (b) Djukic, J.-P.; Maisse, A.; Pfeffer, M.; Dötz, K. H.; Nieger, M. Organometallics 1999, 18, 2786.
-
(1999)
Organometallics
, vol.18
, pp. 2786
-
-
Djukic, J.-P.1
Maisse, A.2
Pfeffer, M.3
Dötz, K.H.4
Nieger, M.5
-
46
-
-
30844460915
-
-
note
-
2 with aldimine, we could not observe the formation of the intermediate.
-
-
-
-
47
-
-
30844446825
-
-
note
-
1H NMR yields of 6 were determined based on dibromomethane as an internal standard.
-
-
-
-
48
-
-
30844438422
-
-
note
-
5 did not promote the formation reaction of 6a.
-
-
-
-
49
-
-
30844439769
-
-
note
-
Under reflux conditions, 6a was obtained irregularly as time passed. That is, yields of 6a were 3% (1 h), 18% (3 h), 95% (8 h), and >99% (24 h), respectively. These results indicate the existence of an induction time to form active species to catalyze the formation reaction of phthalimidine derivatives. However, the structure of the active species is still not clear.
-
-
-
-
50
-
-
30844439050
-
-
note
-
2 in 1,2-dichloroethane in quantitative yield under reflux conditions, the yield decreased to 27% at 70 °C, and the reaction did not proceed at all at 50 °C.
-
-
-
-
51
-
-
0027913099
-
-
In the following reports, compounds derived from double C-H bond activation and insertion of unsaturated molecules at two ortho-positions were obtained as side products: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
-
(1993)
Nature
, vol.366
, pp. 529
-
-
Murai, S.1
Kakiuchi, F.2
Sekine, S.3
Tanaka, Y.4
Kamatani, A.5
Sonoda, M.6
Chatani, N.7
-
52
-
-
0001818455
-
-
(b) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
-
(1995)
Bull. Chem. Soc. Jpn.
, vol.68
, pp. 62
-
-
Kakiuchi, F.1
Sekine, S.2
Tanaka, Y.3
Kamatani, A.4
Sonoda, M.5
Chatani, N.6
Murai, S.7
-
53
-
-
0034966863
-
-
(c) Kakiuchi, F.; Tsujimoto, T.; Sonoda, M.; Chatani, N.; Murai, S. Synlett 2001, 948.
-
(2001)
Synlett
, pp. 948
-
-
Kakiuchi, F.1
Tsujimoto, T.2
Sonoda, M.3
Chatani, N.4
Murai, S.5
-
54
-
-
0035898790
-
-
(d) Lim, Y.-G.; Han, J.-S.; Yang, S.-S.; Chun, J. H. Tetrahedron Lett. 2001, 42, 4853.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 4853
-
-
Lim, Y.-G.1
Han, J.-S.2
Yang, S.-S.3
Chun, J.H.4
-
55
-
-
0035935155
-
-
(e) Lim, Y.-G.; Lee, K.-H.; Koo, B. T.; Kang, J.-B. Tetrahedron Lett. 2001, 42, 7609.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 7609
-
-
Lim, Y.-G.1
Lee, K.-H.2
Koo, B.T.3
Kang, J.-B.4
-
56
-
-
1042266458
-
-
(f) Lim, Y.-G.; Han, J.-S.; Koo, B. T.; Kang, J.-B. J. Mol. Catal. A: 2004, 209, 41.
-
(2004)
J. Mol. Catal. A
, vol.209
, pp. 41
-
-
Lim, Y.-G.1
Han, J.-S.2
Koo, B.T.3
Kang, J.-B.4
-
57
-
-
30844455251
-
-
note
-
2 under reflux conditions, 2-phenylethylisocyanate was recovered quantitatively. Though this result shows that the problems are not in the stability of alkyl isocyanate, the reason is not clear.
-
-
-
-
58
-
-
30844456303
-
-
note
-
The reactivities of aldimines bearing an electron-donating or an electron-withdrawing group toward acetylenes or isocyanates are opposite. The reason for these results is not clear yet.
-
-
-
-
59
-
-
0001818455
-
-
Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62.
-
(1995)
Bull. Chem. Soc. Jpn.
, vol.68
, pp. 62
-
-
Kakiuchi, F.1
Sekine, S.2
Tanaka, Y.3
Kamatani, A.4
Sonoda, M.5
Chatani, N.6
Murai, S.7
-
60
-
-
0000171099
-
-
(a) 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
-
61
-
-
0037184456
-
-
(b) 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
-
62
-
-
11444263216
-
-
(c) Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687.
-
(2004)
Org. Lett.
, vol.6
, pp. 4687
-
-
Lim, S.-G.1
Ahn, J.-A.2
Jun, C.-H.3
-
63
-
-
0037765448
-
-
Du, S.; Kautz, J. A.; McGrath, T. D.; Stone, F. G. A. Organometallics 2003, 22, 2842.
-
(2003)
Organometallics
, vol.22
, pp. 2842
-
-
Du, S.1
Kautz, J.A.2
McGrath, T.D.3
Stone, F.G.A.4
-
68
-
-
0000359668
-
-
Forth, M. A.; Mitchell, M. B.; Smith, S. A. C.; Gombatz, K.; Snyder, L. J. Org. Chem. 1994, 59, 2616.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 2616
-
-
Forth, M.A.1
Mitchell, M.B.2
Smith, S.A.C.3
Gombatz, K.4
Snyder, L.5
-
70
-
-
0000656506
-
-
Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 10520
-
-
Ishihara, K.1
Miyata, M.2
Hattori, K.3
Tada, T.4
Yamamoto, H.5
|