-
3
-
-
77955014834
-
-
For recent examples, see
-
For recent examples, see
-
-
-
-
5
-
-
34147210204
-
-
Saito, T., Sugizaki, K., Otani, T., and Suyama, T. Org. Lett. 2007, 9, 1239
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(2007)
Org. Lett.
, vol.9
, pp. 1239
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Saito, T.1
Sugizaki, K.2
Otani, T.3
Suyama, T.4
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6
-
-
70349320322
-
-
Tanaka, K., Mimura, M., and Hojo, D. Tetrahedron 2009, 65, 9008
-
(2009)
Tetrahedron
, vol.65
, pp. 9008
-
-
Tanaka, K.1
Mimura, M.2
Hojo, D.3
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11
-
-
70349784873
-
-
Yu, R. T., Lee, E. E., Malik, G., and Rovis, T. Angew. Chem., Int. Ed. 2009, 48, 2379-2382
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 2379-2382
-
-
Yu, R.T.1
Lee, E.E.2
Malik, G.3
Rovis, T.4
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13
-
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77955048280
-
-
Oinen, M. E., Yu, R. T., and Rovis, T. Org. Lett. 2009, 12, 4943
-
(2009)
Org. Lett.
, vol.12
, pp. 4943
-
-
Oinen, M.E.1
Yu, R.T.2
Rovis, T.3
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14
-
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70349396091
-
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Yu, R. T., Keller Friedman, R., and Rovis, T. J. Am. Chem. Soc. 2009, 131, 13250
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(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 13250
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Yu, R.T.1
Keller Friedman, R.2
Rovis, T.3
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15
-
-
70350662862
-
-
Dalton, D. M., Oberg, K. M., Yu, R. T., Lee, E. E., Perreault, S., Oinen, M. E., Pease, M. L., Malik, G., and Rovis, T. J. Am. Chem. Soc. 2009, 131, 15717
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(2009)
J. Am. Chem. Soc.
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Dalton, D.M.1
Oberg, K.M.2
Yu, R.T.3
Lee, E.E.4
Perreault, S.5
Oinen, M.E.6
Pease, M.L.7
Malik, G.8
Rovis, T.9
-
17
-
-
77955016847
-
-
For a recent review of rhodium catalyzed C-H activation in C-C bond formation see
-
For a recent review of rhodium catalyzed C-H activation in C-C bond formation see
-
-
-
-
18
-
-
77349090183
-
-
Colby, D. A., Bergman, R. G., and Ellman, J. A. Chem. Rev. 2010, 110, 624
-
(2010)
Chem. Rev.
, vol.110
, pp. 624
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-
Colby, D.A.1
Bergman, R.G.2
Ellman, J.A.3
-
19
-
-
77955032108
-
-
For recent examples, see
-
For recent examples, see
-
-
-
-
20
-
-
43249089367
-
-
Kajita, Y., Matsubara, S., and Kurahashi, T. J. Am. Chem. Soc. 2008, 130, 6058
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 6058
-
-
Kajita, Y.1
Matsubara, S.2
Kurahashi, T.3
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21
-
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52049100181
-
-
Miura, T., Yamachi, M., and Murakami, M. Org. Lett. 2008, 10, 3085
-
(2008)
Org. Lett.
, vol.10
, pp. 3085
-
-
Miura, T.1
Yamachi, M.2
Murakami, M.3
-
22
-
-
77955017273
-
-
For a recent stoichiometric example see
-
For a recent stoichiometric example see
-
-
-
-
23
-
-
51949093660
-
-
Li, L., Brennessel, W. W., and Jones, W. D. J. Am. Chem. Soc. 2008, 130, 12414
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 12414
-
-
Li, L.1
Brennessel, W.W.2
Jones, W.D.3
-
24
-
-
34147156671
-
-
Ueura, K., Satoh, T., and Miura, M. Org. Lett. 2007, 9, 1407
-
(2007)
Org. Lett.
, vol.9
, pp. 1407
-
-
Ueura, K.1
Satoh, T.2
Miura, M.3
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25
-
-
77951788947
-
-
Morimoto, K., Hirano, K., Satoh, T., and 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
-
26
-
-
69249088444
-
-
Fukutani, T., Umeda, N., Hirano, K., Satoh, T., and Miura, M. Chem. Commun. 2009, 5141
-
(2009)
Chem. Commun.
, pp. 5141
-
-
Fukutani, T.1
Umeda, N.2
Hirano, K.3
Satoh, T.4
Miura, M.5
-
27
-
-
47049108951
-
-
Umeda, N., Tsurugi, H., Satoh, T., and Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 4019
-
-
Umeda, N.1
Tsurugi, H.2
Satoh, T.3
Miura, M.4
-
28
-
-
57549086217
-
-
Stuart, D. R., Bertrand-Laperle, M., Burgess, K. M. N., and Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474
-
(2008)
J. Am. Chem. Soc.
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, pp. 16474
-
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Stuart, D.R.1
Bertrand-Laperle, M.2
Burgess, K.M.N.3
Fagnou, K.4
-
29
-
-
69349098824
-
-
For an additional rhodium catalyzed cyclization by Fagnou, see
-
For an additional rhodium catalyzed cyclization by Fagnou, see: Guimond, N. and Fagnou, K. J. Am. Chem. Soc. 2009, 131, 12050
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 12050
-
-
Guimond, N.1
Fagnou, K.2
-
30
-
-
77955018552
-
-
For a review of isoquinolone synthesis, see
-
For a review of isoquinolone synthesis, see
-
-
-
-
32
-
-
43849112641
-
-
This has been suggested in palladium C-H functionalization; see
-
This has been suggested in palladium C-H functionalization; see Lafrance, M., Lapointe, D., and Fagnou, K. Tetrahedron 2008, 64, 6015
-
(2008)
Tetrahedron
, vol.64
, pp. 6015
-
-
Lafrance, M.1
Lapointe, D.2
Fagnou, K.3
-
33
-
-
77955015930
-
-
Similar reactivity was observed by Miura and Satoh when examining 2-aryl oxazole substrates; see ref 8c
-
Similar reactivity was observed by Miura and Satoh when examining 2-aryl oxazole substrates; see ref 8c
-
-
-
-
34
-
-
77955038091
-
-
I -Pr and t -Bu benzamides provide no cycloadduct under these conditions
-
I -Pr and t -Bu benzamides provide no cycloadduct under these conditions
-
-
-
-
35
-
-
77955026434
-
-
N -acyl benzyl amines do not undergo the cycloaddition under these conditions
-
N -acyl benzyl amines do not undergo the cycloaddition under these conditions
-
-
-
-
36
-
-
77955043895
-
-
Under these conditions, N -methylpyridine-3-carboxamide and N,2-dimethyloxazole-4-carboxamide afford cycloadduct in 0% and 8% yield, respectively
-
Under these conditions, N -methylpyridine-3-carboxamide and N,2-dimethyloxazole-4-carboxamide afford cycloadduct in 0% and 8% yield, respectively
-
-
-
-
37
-
-
84855627640
-
-
2 conditions
-
2 conditions
-
-
-
-
38
-
-
77955044089
-
-
Terminal alkynes are not tolerated under the current reaction conditions
-
Terminal alkynes are not tolerated under the current reaction conditions
-
-
-
-
39
-
-
77955034901
-
-
Acetic acid is generated during the course of the reaction and the Cu salt is used as its hydrate, presumably providing the necessary water and acid to lead to hydrolysis of the acetal
-
Acetic acid is generated during the course of the reaction and the Cu salt is used as its hydrate, presumably providing the necessary water and acid to lead to hydrolysis of the acetal
-
-
-
-
40
-
-
77955034059
-
-
This deuteration experiment was also conducted on N- t -Bu benzamide. In the absence of alkyne, no deuterium incorporation was observed after 16 h under these conditions suggesting the sterics of the tert -butyl group negatively affects its ability to metalate by rhodium. This also suggests that metalation occurs on nitrogen rather than oxygen
-
This deuteration experiment was also conducted on N- t -Bu benzamide. In the absence of alkyne, no deuterium incorporation was observed after 16 h under these conditions suggesting the sterics of the tert -butyl group negatively affects its ability to metalate by rhodium. This also suggests that metalation occurs on nitrogen rather than oxygen
-
-
-
-
41
-
-
77955039979
-
-
The apparent reversed regioselectivity in product 3u seems to contradict this model; further studies to address this dichotomy are ongoing
-
The apparent reversed regioselectivity in product 3u seems to contradict this model; further studies to address this dichotomy are ongoing.
-
-
-
-
42
-
-
77955032484
-
-
During the preparation and review of this manuscript, similar and complementary studies leading to isoquinolone synthesis were reported by the groups of Keith Fagnou and Masahiro Miura; see
-
During the preparation and review of this manuscript, similar and complementary studies leading to isoquinolone synthesis were reported by the groups of Keith Fagnou and Masahiro Miura; see
-
-
-
-
43
-
-
77952570693
-
-
Guimond, N., Gouliaras, C., and Fagnou, K. J. Am. Chem. Soc. 2010, 132, 6908
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 6908
-
-
Guimond, N.1
Gouliaras, C.2
Fagnou, K.3
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44
-
-
77954330183
-
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Mochida, S., Umeda, N., Hirano, K., Satoh, T., and Miura, M. Chem. Lett. 2010, 39, 744
-
(2010)
Chem. Lett.
, vol.39
, pp. 744
-
-
Mochida, S.1
Umeda, N.2
Hirano, K.3
Satoh, T.4
Miura, M.5
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