-
1
-
-
17344362973
-
-
For reviews see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157. (f) Catellani, M. Synlett 2003, 298.
-
(1985)
Chem. Rev.
, vol.85
, pp. 245
-
-
Crabtree, R.H.1
-
2
-
-
0033119285
-
-
For reviews see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157. (f) Catellani, M. Synlett 2003, 298.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 870
-
-
Rybtchinski, B.1
Milstein, D.2
-
3
-
-
0002583629
-
-
For reviews see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157. (f) Catellani, M. Synlett 2003, 298.
-
(1999)
Top. Organomet. Chem.
, vol.3
, pp. 97
-
-
Murakami, M.1
Ito, Y.2
-
4
-
-
0038367560
-
-
For reviews see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157. (f) Catellani, M. Synlett 2003, 298.
-
(2002)
Chem. Eur. J.
, vol.8
, pp. 2423
-
-
Jun, C.-H.1
Moon, C.W.2
Lee, D.-Y.3
-
5
-
-
0037121126
-
-
For reviews see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157. (f) Catellani, M. Synlett 2003, 298.
-
(2002)
J. Mol. Catal. A: Chem.
, vol.189
, pp. 157
-
-
Perthuisot, C.1
Edelbach, B.L.2
Zubris, D.L.3
Simhai, N.4
Iverson, C.N.5
Müller, C.6
Satoh, T.7
Jones, W.D.8
-
6
-
-
0037288964
-
-
For reviews see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870. (c) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97. (d) Jun, C.-H.; Moon, C. W.; Lee, D.-Y. Chem. Eur. J. 2002, 8, 2423. (e) Perthuisot, C.; Edelbach, B. L.; Zubris, D. L.; Simhai, N.; Iverson, C. N.; Müller, C.; Satoh, T.; Jones, W. D. J. Mol. Catal. A: Chem. 2002, 189, 157. (f) Catellani, M. Synlett 2003, 298.
-
(2003)
Synlett
, pp. 298
-
-
Catellani, M.1
-
7
-
-
0035944452
-
-
(a) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 10407
-
-
Terao, Y.1
Wakui, H.2
Satoh, T.3
Miura, M.4
Nomura, M.5
-
8
-
-
0038548106
-
-
(b) Terao, Y.; Wakui, H.; Nomoto, N.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236.
-
(2003)
J. Org. Chem.
, vol.68
, pp. 5236
-
-
Terao, Y.1
Wakui, H.2
Nomoto, N.3
Satoh, T.4
Miura, M.5
Nomura, M.6
-
9
-
-
0038637020
-
-
and references therein
-
Pd-catalyzed arylative coupling of alcohols via β-C elimination: (a) Cyclobutanols: Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862 and references therein. (b) 3-Allen-1-ols: Oh, C. H.; Yung, S. H.; Bang, S. Y.; Park, D. I. Org. Lett. 2002, 4, 3325.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 8862
-
-
Matsumura, S.1
Maeda, Y.2
Nishimura, T.3
Uemura, S.4
-
10
-
-
0041307078
-
-
Pd-catalyzed arylative coupling of alcohols via β-C elimination: (a) Cyclobutanols: Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862 and references therein. (b) 3-Allen-1-ols: Oh, C. H.; Yung, S. H.; Bang, S. Y.; Park, D. I. Org. Lett. 2002, 4, 3325.
-
(2002)
Org. Lett.
, vol.4
, pp. 3325
-
-
Oh, C.H.1
Yung, S.H.2
Bang, S.Y.3
Park, D.I.4
-
11
-
-
1342302388
-
-
Other Pd-catalyzed reactions involving β-C elimination via Pd-(II) alcoholate: (a) Account; Nishimura, T.; Uemura, S. Synlett 2004, 201. (b) Harayama, H.; Kuroki, T.; Kimura, M.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2352. (c) Park S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147. (d) Okumoto, H.; Jinnai, T.; Shimizu, H.; Harada, Y.; Mishima, H.; Suzuki, A. Synlett 2000, 629.
-
(2004)
Synlett
, pp. 201
-
-
Nishimura, T.1
Uemura, S.2
-
12
-
-
0030666282
-
-
Other Pd-catalyzed reactions involving β-C elimination via Pd-(II) alcoholate: (a) Account; Nishimura, T.; Uemura, S. Synlett 2004, 201. (b) Harayama, H.; Kuroki, T.; Kimura, M.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2352. (c) Park S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147. (d) Okumoto, H.; Jinnai, T.; Shimizu, H.; Harada, Y.; Mishima, H.; Suzuki, A. Synlett 2000, 629.
-
(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 2352
-
-
Harayama, H.1
Kuroki, T.2
Kimura, M.3
Tanaka, S.4
Tamaru, Y.5
-
13
-
-
0000692217
-
-
Other Pd-catalyzed reactions involving β-C elimination via Pd-(II) alcoholate: (a) Account; Nishimura, T.; Uemura, S. Synlett 2004, 201. (b) Harayama, H.; Kuroki, T.; Kimura, M.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2352. (c) Park S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147. (d) Okumoto, H.; Jinnai, T.; Shimizu, H.; Harada, Y.; Mishima, H.; Suzuki, A. Synlett 2000, 629.
-
(2000)
Org. Lett.
, vol.2
, pp. 147
-
-
Park, S.-B.1
Cha, J.K.2
-
14
-
-
0034128012
-
-
Other Pd-catalyzed reactions involving β-C elimination via Pd-(II) alcoholate: (a) Account; Nishimura, T.; Uemura, S. Synlett 2004, 201. (b) Harayama, H.; Kuroki, T.; Kimura, M.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1997, 36, 2352. (c) Park S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147. (d) Okumoto, H.; Jinnai, T.; Shimizu, H.; Harada, Y.; Mishima, H.; Suzuki, A. Synlett 2000, 629.
-
(2000)
Synlett
, pp. 629
-
-
Okumoto, H.1
Jinnai, T.2
Shimizu, H.3
Harada, Y.4
Mishima, H.5
Suzuki, A.6
-
16
-
-
0000746286
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(1998)
Chem. Commun.
, pp. 1361
-
-
Shaw, B.L.1
Perera, S.D.2
Staley, E.A.3
-
17
-
-
0006458382
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(2001)
J. Chem. Commun.
, pp. 669
-
-
Goossen, L.1
-
18
-
-
33947092885
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2941
-
-
Ziegler Jr., C.B.1
Heck, R.F.2
-
19
-
-
0030760535
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 8451
-
-
Wagaw, S.1
Rennels, R.A.2
Buchwald, S.L.3
-
20
-
-
0000313274
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(1992)
Bull. Soc. Chim. Fr.
, vol.129
, pp. 273
-
-
Friess, B.1
Cazes, B.2
Gore, J.3
-
21
-
-
0001844950
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(1994)
Inorg. Chim. Acta
, vol.222
, pp. 37
-
-
Ollivier, J.1
Dorizon, P.2
Priras, P.P.3
De Meijere, A.4
Salaün, J.5
-
22
-
-
0027991195
-
-
3 in the palladium-catalyzed reaction of organic halides: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Goossen, L. J. Chem. Commun. 2001, 669. (c) Ziegler, C. B., Jr.; Heck R. F. J. Org. Chem. 1978, 43, 2941. (d) Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451. For the reaction of allyl compounds see: (e) Friess, B.; Cazes, B.; Gore, J. Bull. Soc. Chim. Fr. 1992, 129, 273. (f) Ollivier, J.; Dorizon, P.; Priras, P. P.; de Meijere, A.; Salaün, J. Inorg. Chim. Acta 1994, 222, 37. (g) Bienaymé H. Tetrahedron Lett. 1994, 35, 7383.
-
(1994)
Tetrahedron Lett.
, vol.35
, pp. 7383
-
-
Bienaymé, H.1
-
23
-
-
4644330617
-
-
note
-
6a The cyclization process is considered to be reversible under the present conditions.
-
-
-
-
24
-
-
0000379185
-
-
A reviewer has kindly suggested a possibility that intermediate B reversibly reacts with the ketone moiety liberated to regenerate A. Such a nucleophilic arylation of ketones with ArPd(II) species is known to occur intramolecularly: (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827. (b) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. Thus, the selective formation of 13 as well as 12 under the present conditions (Table 2) could be attributed to the reversibility.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 4827
-
-
Quan, L.G.1
Lamrani, M.2
Yamamoto, Y.3
-
25
-
-
0037433240
-
-
A reviewer has kindly suggested a possibility that intermediate B reversibly reacts with the ketone moiety liberated to regenerate A. Such a nucleophilic arylation of ketones with ArPd(II) species is known to occur intramolecularly: (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827. (b) Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J. J. Am. Chem. Soc. 2003, 125, 1587. Thus, the selective formation of 13 as well as 12 under the present conditions (Table 2) could be attributed to the reversibility.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1587
-
-
Solé, D.1
Vallverdú, L.2
Solans, X.3
Font-Bardía, M.4
Bonjoch, J.5
-
26
-
-
0000906974
-
-
ArSn: (a) Cacchi, S.; Misiti, D.; Palmieri, G. Tetrahedron 1981, 37, 2941. (b) Ohe, T.; Uemura, S. Tetrahedron Lett. 2002, 43, 1269.
-
(1981)
Tetrahedron
, vol.37
, pp. 2941
-
-
Cacchi, S.1
Misiti, D.2
Palmieri, G.3
-
27
-
-
0037060018
-
-
ArSn: (a) Cacchi, S.; Misiti, D.; Palmieri, G. Tetrahedron 1981, 37, 2941. (b) Ohe, T.; Uemura, S. Tetrahedron Lett. 2002, 43, 1269.
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 1269
-
-
Ohe, T.1
Uemura, S.2
-
28
-
-
33751156934
-
-
ArB: (a) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shim, S. C. J. Org. Chem. 1995, 60, 883. (b) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. (c) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 883
-
-
Cho, C.S.1
Motofusa, S.2
Ohe, K.3
Uemura, S.4
Shim, S.C.5
-
29
-
-
0037450175
-
-
ArB: (a) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shim, S. C. J. Org. Chem. 1995, 60, 883. (b) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. (c) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 805
-
-
Oh, C.H.1
Jung, H.H.2
Kim, K.S.3
Kim, N.4
-
30
-
-
0037715338
-
-
ArB: (a) Cho, C. S.; Motofusa, S.; Ohe, K.; Uemura, S.; Shim, S. C. J. Org. Chem. 1995, 60, 883. (b) Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805. (c) Nishikata, T.; Yamamoto, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 2768.
-
(2003)
Angew. Chem., Int. Ed.
, vol.42
, pp. 2768
-
-
Nishikata, T.1
Yamamoto, Y.2
Miyaura, N.3
-
31
-
-
0242551501
-
-
ArSi: Nishikata, T.; Yamamoto, Y.; Miyaura, N. Chem. Lett. 2003, 32, 752.
-
(2003)
Chem. Lett.
, vol.32
, pp. 752
-
-
Nishikata, T.1
Yamamoto, Y.2
Miyaura, N.3
|