-
5
-
-
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
-
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
-
-
77149164746
-
-
Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654
-
(2010)
Chem.-Eur. J.
, vol.16
, pp. 2654
-
-
Jazzar, R.1
Hitce, J.2
Renaudat, A.3
Sofack-Kreutzer, J.4
Baudoin, O.5
-
9
-
-
24644495100
-
-
For selected recent references, see: Pastine, S. J.; McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2005, 127, 12180
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 12180
-
-
Pastine, S.J.1
McQuaid, K.M.2
Sames, D.3
-
11
-
-
33746302757
-
-
Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2006, 45, 1683
-
(2006)
Angew. Chem., Int. Ed.
, vol.45
, pp. 1683
-
-
Tobisu, M.1
Chatani, N.2
-
12
-
-
53249123367
-
-
Barluenga, J.; Fananás-Mastral, M.; Aznar, F.; Valdés, C. Angew. Chem., Int. Ed. 2008, 47, 6594
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 6594
-
-
Barluenga, J.1
Fananás-Mastral, M.2
Aznar, F.3
Valdés, C.4
-
14
-
-
67749142078
-
-
Shikanai, D.; Murase, H.; Hata, T.; Urabe, H. J. Am. Chem. Soc. 2009, 131, 3166
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3166
-
-
Shikanai, D.1
Murase, H.2
Hata, T.3
Urabe, H.4
-
15
-
-
70349399209
-
-
Murarka, S.; Deb, I.; Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2009, 131, 13226
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 13226
-
-
Murarka, S.1
Deb, I.2
Zhang, C.3
Seidel, D.4
-
17
-
-
77949395209
-
-
Jurberg, I. D.; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 3543
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 3543
-
-
Jurberg, I.D.1
Odabachian, Y.2
Gagosz, F.3
-
19
-
-
77956081347
-
-
Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 11847
-
-
Kang, Y.K.1
Kim, S.M.2
Kim, D.Y.3
-
20
-
-
77957065022
-
-
These types of reactions have been classified under the term tert -amino effect. For reviews, see: Meth-Cohn, O.; Suschitzky, H. Adv. Heterocycl. Chem. 1972, 14, 211
-
(1972)
Adv. Heterocycl. Chem.
, vol.14
, pp. 211
-
-
Meth-Cohn, O.1
Suschitzky, H.2
-
24
-
-
33748291386
-
-
Matyus, P.; Elias, O.; Tapolcsanyi, P.; Polonka-Balint, A.; Halasz-Dajka, B. Synthesis 2006, 2625
-
(2006)
Synthesis
, pp. 2625
-
-
Matyus, P.1
Elias, O.2
Tapolcsanyi, P.3
Polonka-Balint, A.4
Halasz-Dajka, B.5
-
25
-
-
0344626623
-
-
Verboom, W.; Reinhoudt, D. N.; Visser, R.; Harkema, S. J. Org. Chem. 1984, 49, 269
-
(1984)
J. Org. Chem.
, vol.49
, pp. 269
-
-
Verboom, W.1
Reinhoudt, D.N.2
Visser, R.3
Harkema, S.4
-
26
-
-
0012118604
-
-
Nijhuis, W. H. N.; Verboom, W.; Reinhoudt, D. N.; Harkema, S. J. Am. Chem. Soc. 1987, 109, 3136
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 3136
-
-
Nijhuis, W.H.N.1
Verboom, W.2
Reinhoudt, D.N.3
Harkema, S.4
-
28
-
-
79952260757
-
-
Groenen, L. C.; Verboom, W.; Nijhuis, W. H. N.; Reinhoudt, D. N.; Van Hummel, G. J.; Feil, D. Tetrahedron 1988, 44, 4627
-
(1988)
Tetrahedron
, vol.44
, pp. 4627
-
-
Groenen, L.C.1
Verboom, W.2
Nijhuis, W.H.N.3
Reinhoudt, D.N.4
Van Hummel, G.J.5
Feil, D.6
-
29
-
-
0024597364
-
-
Nijhuis, W. H. N.; Verboom, W.; Abu El-Fadl, A.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 199
-
(1989)
J. Org. Chem.
, vol.54
, pp. 199
-
-
Nijhuis, W.H.N.1
Verboom, W.2
Abu El-Fadl, A.3
Harkema, S.4
Reinhoudt, D.N.5
-
30
-
-
0024489430
-
-
Nijhuis, W. H. N.; Verboom, W.; Abu El-Fadl, A.; Van Hummel, G. J.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 209
-
(1989)
J. Org. Chem.
, vol.54
, pp. 209
-
-
Nijhuis, W.H.N.1
Verboom, W.2
Abu El-Fadl, A.3
Van Hummel, G.J.4
Reinhoudt, D.N.5
-
31
-
-
0032576855
-
-
Ojea, V.; Muinelo, I.; Quintela, J. M. Tetrahedron 1998, 54, 927
-
(1998)
Tetrahedron
, vol.54
, pp. 927
-
-
Ojea, V.1
Muinelo, I.2
Quintela, J.M.3
-
32
-
-
23944461239
-
-
Kaval, N.; Halasz-Dajka, B.; Vo-Thanh, G.; Dehaen, W.; Van der Eycken, J.; Matyus, P.; Loupy, A.; Van der Eycken, E. Tetrahedron 2005, 61, 9052
-
(2005)
Tetrahedron
, vol.61
, pp. 9052
-
-
Kaval, N.1
Halasz-Dajka, B.2
Vo-Thanh, G.3
Dehaen, W.4
Van Der Eycken, J.5
Matyus, P.6
Loupy, A.7
Van Der Eycken, E.8
-
33
-
-
56849106003
-
-
Polonka-Bálint, A.; Saraceno, C.; Ludányi, K.; Bényei, A.; Mátyus, P. Synlett 2008, 2846
-
(2008)
Synlett
, pp. 2846
-
-
Polonka-Bálint, A.1
Saraceno, C.2
Ludányi, K.3
Bényei, A.4
Mátyus, P.5
-
34
-
-
59649112358
-
-
Murarka, S.; Zhang, C.; Konieczynska, M. D.; Seidel, D. Org. Lett. 2009, 11, 129
-
(2009)
Org. Lett.
, vol.11
, pp. 129
-
-
Murarka, S.1
Zhang, C.2
Konieczynska, M.D.3
Seidel, D.4
-
35
-
-
58149293587
-
-
Zhang, C.; Murarka, S.; Seidel, D. J. Org. Chem. 2009, 74, 419
-
(2009)
J. Org. Chem.
, vol.74
, pp. 419
-
-
Zhang, C.1
Murarka, S.2
Seidel, D.3
-
36
-
-
67749147313
-
-
Ruble, J. C.; Hurd, A. R.; Johnson, T. A.; Sherry, D. A.; Barbachyn, M. R.; Toogood, P. L.; Bundy, G. L.; Graber, D. R.; Kamilar, G. M. J. Am. Chem. Soc. 2009, 131, 3991
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 3991
-
-
Ruble, J.C.1
Hurd, A.R.2
Johnson, T.A.3
Sherry, D.A.4
Barbachyn, M.R.5
Toogood, P.L.6
Bundy, G.L.7
Graber, D.R.8
Kamilar, G.M.9
-
37
-
-
67650311554
-
-
McQuaid, K. M.; Long, J. Z.; Sames, D. Org. Lett. 2009, 11, 2972
-
(2009)
Org. Lett.
, vol.11
, pp. 2972
-
-
McQuaid, K.M.1
Long, J.Z.2
Sames, D.3
-
38
-
-
67650473037
-
-
Mori, K.; Ohshima, Y.; Ehara, K.; Akiyama, T. Chem. Lett. 2009, 38, 524
-
(2009)
Chem. Lett.
, vol.38
, pp. 524
-
-
Mori, K.1
Ohshima, Y.2
Ehara, K.3
Akiyama, T.4
-
39
-
-
77951158758
-
-
Mori, K.; Kawasaki, T.; Sueoka, S.; Akiyama, T. Org. Lett. 2010, 12, 1732
-
(2010)
Org. Lett.
, vol.12
, pp. 1732
-
-
Mori, K.1
Kawasaki, T.2
Sueoka, S.3
Akiyama, T.4
-
40
-
-
68049099258
-
-
Tobisu, M.; Nakai, H.; Chatani, N. J. Org. Chem. 2009, 74, 5471
-
(2009)
J. Org. Chem.
, vol.74
, pp. 5471
-
-
Tobisu, M.1
Nakai, H.2
Chatani, N.3
-
41
-
-
70349783659
-
-
Yang, S.; Li, Z.; Jian, X.; He, C. Angew. Chem., Int. Ed. 2009, 48, 3999
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 3999
-
-
Yang, S.1
Li, Z.2
Jian, X.3
He, C.4
Mahoney, S.J.5
Moon, D.T.6
Hollinger, J.7
Fillion, E.8
Bajracharya, G.B.9
Pahadi, N.K.10
Gridnev, I.D.11
Yamamoto, Y.12
-
42
-
-
67649342031
-
-
For another benzylic hydride shift/ring closure for the formation of tetraline derivatives, see: Mahoney, S. J.; Moon, D. T.; Hollinger, J.; Fillion, E. Tetrahedron Lett. 2009, 50, 4706
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 4706
-
-
-
43
-
-
33746905548
-
-
For hydride shifts from di- and/or triarylmethane, see: Bajracharya, G. B.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2006, 71, 6204
-
(2006)
J. Org. Chem.
, vol.71
, pp. 6204
-
-
-
44
-
-
77957673072
-
-
Alajarin, M.; Bonillo, B.; Ortin, M.-M.; Sanchez-Andrada, P.; Vidal, A.; Orenes, R.-A. Org. Biomol. Chem. 2010, 8, 4690
-
(2010)
Org. Biomol. Chem.
, vol.8
, pp. 4690
-
-
Alajarin, M.1
Bonillo, B.2
Ortin, M.-M.3
Sanchez-Andrada, P.4
Vidal, A.5
Orenes, R.-A.6
-
45
-
-
0020782543
-
-
For examples of [1,6]-hydride shift-mediated C-H functionalization, see: Reinhoudt, D. N.; Visser, G. W.; Verboom, W.; Benders, P. H.; Pennings, M. L. M. J. Am. Chem. Soc. 1983, 105, 4775
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 4775
-
-
Reinhoudt, D.N.1
Visser, G.W.2
Verboom, W.3
Benders, P.H.4
Pennings, M.L.M.5
-
46
-
-
0028284171
-
-
De Boeck, B.; Jiang, S.; Janousek, Z.; Viehe, H. G. Tetrahedron 1994, 50, 7075
-
(1994)
Tetrahedron
, vol.50
, pp. 7075
-
-
De Boeck, B.1
Jiang, S.2
Janousek, Z.3
Viehe, H.G.4
-
47
-
-
0028882631
-
-
De Boeck, B.; Janousek, Z.; Viehe, H. G. Tetrahedron 1995, 51, 13239
-
(1995)
Tetrahedron
, vol.51
, pp. 13239
-
-
De Boeck, B.1
Janousek, Z.2
Viehe, H.G.3
-
48
-
-
40149096724
-
-
Zhang, C.; Kanta De, C.; Mal, R.; Seidel, D. J. Am. Chem. Soc. 2008, 130, 416
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 416
-
-
Zhang, C.1
De, K.C.2
Mal, R.3
Seidel, D.4
-
49
-
-
52949141872
-
-
Che, X.; Sheng, L.; Dang, Q.; Bai, X. Synlett 2008, 2373
-
(2008)
Synlett
, pp. 2373
-
-
Che, X.1
Sheng, L.2
Dang, Q.3
Bai, X.4
-
50
-
-
77956053142
-
-
Földi, A. A.; Ludányi, K.; Bényei, A. C.; Mátyus, P. Synlett 2010, 2109
-
(2010)
Synlett
, pp. 2109
-
-
Földi, A.A.1
Ludányi, K.2
Bényei, A.C.3
Mátyus, P.4
-
51
-
-
79952254325
-
-
3, see refs 2a, 2j, 4j, 4m, 6, and 7c.
-
3, see refs 2a, 2j, 4j, 4m, 6, and 7c.
-
-
-
-
52
-
-
79952268622
-
-
In order to obtain information about the reaction course, some D-labeling experiments were conducted. The results are described in the Supporting Information.
-
In order to obtain information about the reaction course, some D-labeling experiments were conducted. The results are described in the Supporting Information.
-
-
-
-
53
-
-
79952273324
-
-
For a theoretical study of the effect of the substituent on the stability of a carbocation, see: El-Nahas, A. M.; Clark, T. J. Org. Chem. 1995, 60, 6024
-
(1995)
J. Org. Chem.
, vol.60
, pp. 6024
-
-
El-Nahas, A.M.1
Clark, T.2
-
54
-
-
79952258500
-
-
We assumed that there are two factors contributing to the predominant formation of a five-membered ring over a seven-membered ring: (1) Baldwin's rule and (2) steric repulsion between the bulky barbituric acid moiety and the dimethyl group around the tertiary carbocation in the transition state for the formation of a seven-membered ring.
-
We assumed that there are two factors contributing to the predominant formation of a five-membered ring over a seven-membered ring: (1) Baldwin's rule and (2) steric repulsion between the bulky barbituric acid moiety and the dimethyl group around the tertiary carbocation in the transition state for the formation of a seven-membered ring.
-
-
-
-
55
-
-
79952271406
-
-
Zhou and Zhang reported a gold-catalyzed internal redox reaction involving C-C bond formation between a furanyl anion species and a carbocation generated by the hydride shift (see ref 2j).
-
Zhou and Zhang reported a gold-catalyzed internal redox reaction involving C-C bond formation between a furanyl anion species and a carbocation generated by the hydride shift (see ref 2j).
-
-
-
-
56
-
-
79952269910
-
-
2Cl (1.0 mL) at refluxing temperature.
-
2Cl (1.0 mL) at refluxing temperature.
-
-
-
-
57
-
-
79952268235
-
-
One of the reviewers suggested the intermolecular hydride shift mechanism. The crossover experiment of d - 3g and a naphthyl-type substrate revealed that the hydride shift occurred intramolecularly. For more detailed information, see the Supporting Information. We thank the reviewer for the suggestion of this experiment.
-
One of the reviewers suggested the intermolecular hydride shift mechanism. The crossover experiment of d-3g and a naphthyl-type substrate revealed that the hydride shift occurred intramolecularly. For more detailed information, see the Supporting Information. We thank the reviewer for the suggestion of this experiment.
-
-
-
|