-
1
-
-
0001551026
-
-
(a) Mizoroki, T.; Mori, K.; Ozawa, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
-
(1971)
Bull. Chem. Soc. Jpn.
, vol.44
, pp. 581
-
-
Mizoroki, T.1
Mori, K.2
Ozawa, A.3
-
3
-
-
0000702671
-
-
Dauben, W. G., Ed.; Wiley: New York
-
Reviews: (a) Heck, R. F. In Organic Reactions; Dauben, W. G., Ed.; Wiley: New York, 1982; Vol. 27, p 345.
-
(1982)
Organic Reactions
, vol.27
, pp. 345
-
-
Heck, R.F.1
-
5
-
-
0000134380
-
-
Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
-
(c) Söderberg, B. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 241.
-
(1995)
Comprehensive Organometallic Chemistry II
, vol.12
, pp. 241
-
-
Söderberg, B.C.1
-
8
-
-
0030995738
-
-
Reviews for the asymmetric version: (f) Shibasaki, M.; Boden, C. D. J.; Kojima, A. Tetrahedron 1997, 53, 7371.
-
(1997)
Tetrahedron
, vol.53
, pp. 7371
-
-
Shibasaki, M.1
Boden, C.D.J.2
Kojima, A.3
-
9
-
-
4143054881
-
-
(g) Loiseleur, M.; Hayashi, M.; Keenan, M.; Schmees, N.; Pfaltz, A. J. Organomet. Chem. 1999, 576, 1.
-
(1999)
J. Organomet. Chem.
, vol.576
, pp. 1
-
-
Loiseleur, M.1
Hayashi, M.2
Keenan, M.3
Schmees, N.4
Pfaltz, A.5
-
11
-
-
0012857368
-
-
Overman, L. E., Ed.; Wiley: New York
-
(a) Link, J. T. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2003; Vol. 60, p 157.
-
(2003)
Organic Reactions
, vol.60
, pp. 157
-
-
Link, J.T.1
-
14
-
-
0001232903
-
-
(d) Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813.
-
(1992)
Pure Appl. Chem.
, vol.64
, pp. 1813
-
-
Overman, L.E.1
Abelman, M.M.2
Kucera, D.J.3
Tran, V.D.4
Ricca, D.J.5
-
16
-
-
33748647785
-
-
(f) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
-
(1994)
Angew. Chem., Int. Ed. Engl.
, vol.33
, pp. 2379
-
-
De Meijere, A.1
Meyer, F.E.2
-
17
-
-
7044235861
-
-
(g) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
-
(1996)
Chem. Rev.
, vol.96
, pp. 365
-
-
Negishi, E.1
Copéret, C.2
Ma, S.3
Liou, S.-Y.4
Liu, F.5
-
18
-
-
0000463815
-
-
(h) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
-
(1996)
Chem. Rev.
, vol.96
, pp. 635
-
-
Ojima, I.1
Tzamarioudaki, M.2
Li, Z.3
Donovan, R.J.4
-
22
-
-
0034637529
-
-
(l) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959.
-
(2000)
Tetrahedron.
, vol.56
, pp. 5959
-
-
Poli, G.1
Giambastiani, G.2
Heumann, A.3
-
25
-
-
33750173220
-
-
(c) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
-
(1993)
Angew. Chem., Int. Ed. Engl.
, vol.32
, pp. 131
-
-
Tietze, L.F.1
Beifuss, U.2
-
32
-
-
0036298510
-
-
(e) Montgomery, J.; Amarasinghe, K. K. D.; Chowdhury, S. K.; Oblinger, E.; Seo, J.; Savchenko, A. V. Pure Appl. Chem. 2002, 74, 129.
-
(2002)
Pure Appl. Chem.
, vol.74
, pp. 129
-
-
Montgomery, J.1
Amarasinghe, K.K.D.2
Chowdhury, S.K.3
Oblinger, E.4
Seo, J.5
Savchenko, A.V.6
-
33
-
-
0242710784
-
-
(f) Miller, K. M.; Molinaro, C.; Jamison, T. F. Tetrahedron: Asymmetry 2003, 14, 3619.
-
(2003)
Tetrahedron: Asymmetry
, vol.14
, pp. 3619
-
-
Miller, K.M.1
Molinaro, C.2
Jamison, T.F.3
-
35
-
-
0025251463
-
-
For the C-bound nickel enolate, see: (a) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30.
-
(1990)
Organometallics
, vol.9
, pp. 30
-
-
Burkhardt, E.R.1
Bergman, R.G.2
Heathcock, C.H.3
-
36
-
-
0035809288
-
-
For related works of the nickel-promoted domino reaction, Montgomery recently reported generation and characterization of the O-bound nickel enolate. See: (b) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
-
(2001)
Organometallics
, vol.20
, pp. 370
-
-
Amarasinghe, K.K.D.1
Chowdhury, S.K.2
Heeg, M.J.3
Montgomery, J.4
-
37
-
-
0242330786
-
-
(c) Mahandru, G. M.; Skauge, A. R. L.; Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 13481. The O-enolate, which is generated by the oxidative cyclization of an enal and alkyne with Ni (O) species, contains a cis double bond in a seven-membered ring. However, a metalacycle generated by a cyclic enone such as 2-cyclopenten-1-one and alkyne with Ni (O) would not be the corresponding O-enolate, because the enolate contains a strained trans double bond in the seven-membered ring.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 13481
-
-
Mahandru, G.M.1
Skauge, A.R.L.2
Chowdhury, S.K.3
Amarasinghe, K.K.D.4
Heeg, M.J.5
Montgomery, J.6
-
39
-
-
0033585539
-
-
For an example of the [2 + 2 + 2] cycloaddition of alkynyl enones with activated alkenes via nickellacycle, see: Seo, J.; Chui, H. M. P.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 476
-
-
Seo, J.1
Chui, H.M.P.2
Heeg, M.J.3
Montgomery, J.4
-
40
-
-
0037120880
-
-
A portion of this work has been previously communicated. See: Ikeda, S.; Miyashita, H.; Taniguchi, M.; Kondo, H.; Okano, M.; Sato, Y.; Odashima, K. J. Am. Chem. Soc. 2002, 124, 12060.
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 12060
-
-
Ikeda, S.1
Miyashita, H.2
Taniguchi, M.3
Kondo, H.4
Okano, M.5
Sato, Y.6
Odashima, K.7
-
41
-
-
4143063762
-
-
note
-
3N was added in the absence of zinc dust, the Ni-catalyzed reaction did not proceed. In contrast, in the Pd-catalyzed Mizoroki-Heck reaction, it is well-known that a variety of bases promote the regeneration of Pd(0) from H-Pd-X species generated by β-hydrogen elimination. See refs 1-3.
-
-
-
-
42
-
-
84958133964
-
-
Negishi and co-workers reported the similar processes in the Pd-catalyzed arylation and alkenylation of enynes. See: Owczarczyk, Z.; Lamaty, F.; Vawter, E. J.; Negishi, E. J. Am. Chem. Soc. 1992, 114, 10091.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10091
-
-
Owczarczyk, Z.1
Lamaty, F.2
Vawter, E.J.3
Negishi, E.4
-
43
-
-
0001150096
-
-
For the β-carbon vs β-hydrogen elimination of 7 and 8, Miller and co-workers reported that the nickel-catalyzed skeletal rearrangement of i to iv was consistent with a mechanism that involved the β-carbon elimination of a complex iii induced by the cyclopropanation of ii.12a However, product v derived from the β-hydrogen elimination of iii was not obtained. On the other hand, they also reported that the same nickel complex catalyzed the rearrangement of v to iv.12b This result suggests that a rapid equilibrium is present between iii and v. In a similar manner, the presence of rapid equilibrium between 7 (or 8) and 10 (and/or 11) cannot be ruled out. (a) Pinke, P. A.; Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4221.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 4221
-
-
Pinke, P.A.1
Miller, R.G.2
-
44
-
-
0010883021
-
-
(b) Pinke, P. A.; Stauffer, R. D.; Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4229
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 4229
-
-
Pinke, P.A.1
Stauffer, R.D.2
Miller, R.G.3
-
45
-
-
0000938189
-
-
Whereas a half-life of 30 h at 27 °C and an activation energy of ca. 26 kcal/mol were characteristic of the equilibration of homoallyl Grignard reagent,13a the half-life for the nickel-catalyzed conversion of i to isomeric products such as iv was <2 min at 25 °C.13b (a) Howden, M. E. H.; Maerker, A.; Burdon, J.; Roberts, J. D. J. Am. Chem. Soc. 1966, 88, 1732.
-
(1966)
J. Am. Chem. Soc.
, vol.88
, pp. 1732
-
-
Howden, M.E.H.1
Maerker, A.2
Burdon, J.3
Roberts, J.D.4
-
46
-
-
0000824684
-
-
(b) Miller, R. G.; Pinke, P. A.; Stauffer, R. D.; Golden, H. J.; Baker, D. J. J. Am. Chem. Soc. 1974, 96, 4211.
-
(1974)
J. Am. Chem. Soc.
, vol.96
, pp. 4211
-
-
Miller, R.G.1
Pinke, P.A.2
Stauffer, R.D.3
Golden, H.J.4
Baker, D.J.5
-
48
-
-
4143124587
-
-
note
-
The reaction took place at room temperature for 3 days and gave 26 in 12% yield along with some unidentified products.
-
-
-
-
50
-
-
0010736039
-
-
For the Ni-catalyzed "Mizoroki-Heck"-type reaction, see: (a) Mori, M.; Ban, Y. Tetrahedron Lett. 1976, 1803.
-
(1976)
Tetrahedron Lett.
, pp. 1803
-
-
Mori, M.1
Ban, Y.2
-
52
-
-
37049095646
-
-
(c) Mori, M.; Kudo, S.; Ban, Y. J. Chem. Soc., Perkin Trans. 1 1979, 771.
-
(1979)
J. Chem. Soc., Perkin Trans. 1
, pp. 771
-
-
Mori, M.1
Kudo, S.2
Ban, Y.3
-
53
-
-
0001529503
-
-
(d) Lebedev, S. A.; Lopatina, V. S.; Petrov, E. S.; Beletskaya, I. P. J. Organomet. Chem. 1988, 344, 253.
-
(1988)
J. Organomet. Chem.
, vol.344
, pp. 253
-
-
Lebedev, S.A.1
Lopatina, V.S.2
Petrov, E.S.3
Beletskaya, I.P.4
-
54
-
-
0029557965
-
-
For Ni-mediated reactions, see: (e) Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1995, 117, 11017.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11017
-
-
Bonjoch, J.1
Solé, D.2
Bosch, J.3
-
55
-
-
0000565043
-
-
Also see: (f) Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 12133
-
-
Solé, D.1
Cancho, Y.2
Llebaria, A.3
Moretó, J.M.4
Delgado, A.5
-
56
-
-
0000960319
-
-
(g) Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Org. Chem. 1996, 61, 5895.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 5895
-
-
Solé, D.1
Cancho, Y.2
Llebaria, A.3
Moretó, J.M.4
Delgado, A.5
-
57
-
-
0032510203
-
-
(h) Cancho, Y.; Martínez, M.; Liebaria, A.; Moretó, J. M.; Delgado, A. Tetrahedron 1998, 54, 1221.
-
(1998)
Tetrahedron
, vol.54
, pp. 1221
-
-
Cancho, Y.1
Martínez, M.2
Liebaria, A.3
Moretó, J.M.4
Delgado, A.5
|