메뉴 건너뛰기




Volumn 62, Issue 8, 1997, Pages 2604-2610

Ru3(CO)12-Catalyzed Reaction of Pyridylbenzenes with Monoxide and Olefins. Carbonylation at a C-H Bond in the Benzene Ring

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001566828     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970131r     Document Type: Article
Times cited : (151)

References (72)
  • 1
    • 0003829345 scopus 로고
    • Plenum Press: New York
    • For recent reviews on carbonylation, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Tkatchenko, I. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; pp 101-223.
    • (1991) Carbonylation
    • Colquhoun, H.M.1    Thompson, D.J.2    Twigg, M.V.3
  • 2
    • 84942772095 scopus 로고
    • Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford
    • For recent reviews on carbonylation, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation; Plenum Press: New York, 1991. Tkatchenko, I. Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; pp 101-223.
    • (1982) Comprehensive Organometallic Chemistry , pp. 101-223
    • Tkatchenko, I.1
  • 5
    • 0000306555 scopus 로고
    • Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. Uemura, S.; Takahashi, H.; Ohe, K.; Sugita, N. J. Organomet. Chem. 1989, 361, 63.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2609
    • Antebi, S.1    Alper, H.2
  • 7
    • 1542684108 scopus 로고
    • Miyaura, N.; Suzuki, A. Chem. Lett. 1981, 879. Cho, C. S.; Ohe, K.; Uemura, S. J. Organomet. Chem. 1995, 496, 221.
    • (1981) Chem. Lett. , vol.879
    • Miyaura, N.1    Suzuki, A.2
  • 10
    • 33947305793 scopus 로고
    • Barlow, L. R.; Davidson, J. M. Chem. Ind. 1965, 1656. Heck, R. F. J. Am. Chem. Soc. 1986, 90, 5546.
    • (1986) J. Am. Chem. Soc. , vol.90 , pp. 5546
    • Heck, R.F.1
  • 11
    • 0001008345 scopus 로고
    • Larock, R. C.; Fellows, C. A. J. Org. Chem. 1980, 45, 363. Larock, R. C.; Fellows, C. A. J. Am. Chem. Soc. 1982, 104, 1900.
    • (1980) J. Org. Chem. , vol.45 , pp. 363
    • Larock, R.C.1    Fellows, C.A.2
  • 14
    • 0007202461 scopus 로고
    • For Pd(II)-catalyzed carbonylation of a benzene ring, see: Fujiwara, Y.; Kawauchi, T.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1980, 220. Taniguchi, Y.; Yamaoka, Y.; Nakata, K.; Takai, K.; Fujiwara, Y. Chem. Lett. 1995, 345. For a recent review, see: Fujiwara, Y.; Takaki, K.; Taniguchi, Y. Synlett 1996, 591.
    • (1980) J. Chem. Soc., Chem. Commun. , vol.220
    • Fujiwara, Y.1    Kawauchi, T.2    Taniguchi, H.3
  • 15
    • 1542789356 scopus 로고
    • For Pd(II)-catalyzed carbonylation of a benzene ring, see: Fujiwara, Y.; Kawauchi, T.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1980, 220. Taniguchi, Y.; Yamaoka, Y.; Nakata, K.; Takai, K.; Fujiwara, Y. Chem. Lett. 1995, 345. For a recent review, see: Fujiwara, Y.; Takaki, K.; Taniguchi, Y. Synlett 1996, 591.
    • (1995) Chem. Lett. , vol.345
    • Taniguchi, Y.1    Yamaoka, Y.2    Nakata, K.3    Takai, K.4    Fujiwara, Y.5
  • 16
    • 0001366689 scopus 로고    scopus 로고
    • For Pd(II)-catalyzed carbonylation of a benzene ring, see: Fujiwara, Y.; Kawauchi, T.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1980, 220. Taniguchi, Y.; Yamaoka, Y.; Nakata, K.; Takai, K.; Fujiwara, Y. Chem. Lett. 1995, 345. For a recent review, see: Fujiwara, Y.; Takaki, K.; Taniguchi, Y. Synlett 1996, 591.
    • (1996) Synlett , pp. 591
    • Fujiwara, Y.1    Takaki, K.2    Taniguchi, Y.3
  • 17
    • 0001759924 scopus 로고
    • For recent examples of transition metal-catalyzed carbonylative cyclization, see: Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. Ishii, Y.; Hidai, M. J. Organomet. Chem. 1992, 428, 279. Takeuchi, R.; Yasue, H. J. Org Chem. 1993, 58, 5386. Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
    • (1991) Organometallics , vol.10 , pp. 508
    • Joh, T.1    Doyama, K.2    Fujiwara, K.3    Maeshima, K.4    Takahashi, S.5
  • 18
    • 1542474669 scopus 로고
    • For recent examples of transition metal-catalyzed carbonylative cyclization, see: Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. Ishii, Y.; Hidai, M. J. Organomet. Chem. 1992, 428, 279. Takeuchi, R.; Yasue, H. J. Org Chem. 1993, 58, 5386. Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
    • (1992) J. Organomet. Chem. , vol.428 , pp. 279
    • Ishii, Y.1    Hidai, M.2
  • 19
    • 0000700253 scopus 로고
    • For recent examples of transition metal-catalyzed carbonylative cyclization, see: Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. Ishii, Y.; Hidai, M. J. Organomet. Chem. 1992, 428, 279. Takeuchi, R.; Yasue, H. J. Org Chem. 1993, 58, 5386. Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
    • (1993) J. Org Chem. , vol.58 , pp. 5386
    • Takeuchi, R.1    Yasue, H.2
  • 20
    • 0000386089 scopus 로고    scopus 로고
    • For recent examples of transition metal-catalyzed carbonylative cyclization, see: Joh, T.; Doyama, K.; Fujiwara, K.; Maeshima, K.; Takahashi, S. Organometallics 1991, 10, 508. Ishii, Y.; Hidai, M. J. Organomet. Chem. 1992, 428, 279. Takeuchi, R.; Yasue, H. J. Org Chem. 1993, 58, 5386. Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
    • (1996) J. Org. Chem. , vol.61 , pp. 6941
    • Kokubo, K.1    Matsumasa, K.2    Miura, M.3    Nomura, M.4
  • 22
    • 0000566918 scopus 로고
    • Fisher, B. J.; Eisenberg, R. Organometallics 1983, 2, 764. Kunin, A. J.; Eisenberg, R. J. Am. Chem. Soc. 1986, 108, 535. Kunin, A. J.; Eisenberg, R. Organometallics 1988, 7, 2124. Gordon, E. M.; Eisenberg, R. J. Mol. Catal. 1988, 45, 57.
    • (1983) Organometallics , vol.2 , pp. 764
    • Fisher, B.J.1    Eisenberg, R.2
  • 23
    • 0001222871 scopus 로고
    • Fisher, B. J.; Eisenberg, R. Organometallics 1983, 2, 764. Kunin, A. J.; Eisenberg, R. J. Am. Chem. Soc. 1986, 108, 535. Kunin, A. J.; Eisenberg, R. Organometallics 1988, 7, 2124. Gordon, E. M.; Eisenberg, R. J. Mol. Catal. 1988, 45, 57.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 535
    • Kunin, A.J.1    Eisenberg, R.2
  • 24
    • 0000287825 scopus 로고
    • Fisher, B. J.; Eisenberg, R. Organometallics 1983, 2, 764. Kunin, A. J.; Eisenberg, R. J. Am. Chem. Soc. 1986, 108, 535. Kunin, A. J.; Eisenberg, R. Organometallics 1988, 7, 2124. Gordon, E. M.; Eisenberg, R. J. Mol. Catal. 1988, 45, 57.
    • (1988) Organometallics , vol.7 , pp. 2124
    • Kunin, A.J.1    Eisenberg, R.2
  • 25
    • 0023996050 scopus 로고
    • Fisher, B. J.; Eisenberg, R. Organometallics 1983, 2, 764. Kunin, A. J.; Eisenberg, R. J. Am. Chem. Soc. 1986, 108, 535. Kunin, A. J.; Eisenberg, R. Organometallics 1988, 7, 2124. Gordon, E. M.; Eisenberg, R. J. Mol. Catal. 1988, 45, 57.
    • (1988) J. Mol. Catal. , vol.45 , pp. 57
    • Gordon, E.M.1    Eisenberg, R.2
  • 26
    • 1542579317 scopus 로고
    • Sakakura, T.; Tanaka, M. Chem. Lett. 1987, 249. Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221.
    • (1987) Chem. Lett. , vol.249
    • Sakakura, T.1    Tanaka, M.2
  • 27
    • 0347164235 scopus 로고
    • Sakakura, T.; Tanaka, M. Chem. Lett. 1987, 249. Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221.
    • (1987) J. Chem. Soc., Chem. Commun. , vol.758
    • Sakakura, T.1    Tanaka, M.2
  • 33
    • 0002459096 scopus 로고
    • Bruce, M. I. Angew. Chem., Int. Ed. Engl. 1977, 16, 73. Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451. Ryabov, A. D. Chem. Rev. 1990, 90, 403.
    • (1977) Angew. Chem., Int. Ed. Engl. , vol.16 , pp. 73
    • Bruce, M.I.1
  • 35
    • 0042728760 scopus 로고
    • Bruce, M. I. Angew. Chem., Int. Ed. Engl. 1977, 16, 73. Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451. Ryabov, A. D. Chem. Rev. 1990, 90, 403.
    • (1990) Chem. Rev. , vol.90 , pp. 403
    • Ryabov, A.D.1
  • 50
    • 85024298320 scopus 로고
    • Usefulness of a pyridine ring as a directing group for formation of C-C bond has been described. Murai, S. J. Synth. Org. Chem. Jpn. 1994, 52, 992.
    • (1994) J. Synth. Org. Chem. Jpn. , vol.52 , pp. 992
    • Murai, S.1
  • 51
    • 37049079695 scopus 로고
    • Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 2267
    • Lim, Y.-G.1    Kim, Y.H.2    Kang, J.-B.3
  • 52
    • 33748986893 scopus 로고    scopus 로고
    • Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 2201
    • Lim, Y.-G.1    Kim, Y.H.2    Kang, J.-B.3
  • 53
    • 0001901115 scopus 로고    scopus 로고
    • Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 585
    • Lim, Y.-G.1    Kang, J.-B.2    Kim, Y.H.3
  • 54
    • 0030369119 scopus 로고    scopus 로고
    • Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Chem. Commun. 1994, 2267. Lim, Y.-G.; Kim, Y. H.; Kang, J.-B. J. Chem. Soc., Perkin Trans. 1 1996, 2201. Lim, Y.-G.; Kang, J.-B.; Kim, Y. H. J. Chem. Soc., Chem. Commun. 1996, 585. Fujii, N.; Kakiuchi, F.; Chatani, N.; Murai, S. Chem. Lett. 1996, 939.
    • (1996) Chem. Lett. , pp. 939
    • Fujii, N.1    Kakiuchi, F.2    Chatani, N.3    Murai, S.4
  • 55
    • 33748975453 scopus 로고
    • Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1603. Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. J. Organomet. Chem. 1995, 492, 87. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Westernacher, S.; Kisch, H. Monatsh. Chem. 1996, 127, 469.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1603
    • Halbritter, G.1    Knoch, F.2    Wolski, A.3    Kish, H.4
  • 56
    • 0003136878 scopus 로고
    • Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1603. Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. J. Organomet. Chem. 1995, 492, 87. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Westernacher, S.; Kisch, H. Monatsh. Chem. 1996, 127, 469.
    • (1995) J. Organomet. Chem. , vol.492 , pp. 87
    • Halbritter, G.1    Knoch, F.2    Wolski, A.3    Kish, H.4
  • 57
    • 0000961051 scopus 로고
    • Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1603. Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. J. Organomet. Chem. 1995, 492, 87. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Westernacher, S.; Kisch, H. Monatsh. Chem. 1996, 127, 469.
    • (1995) Organometallics , vol.14 , pp. 3385
    • Aulwurm, U.R.1    Melchinger, J.U.2    Kisch, H.3
  • 58
    • 0011826420 scopus 로고    scopus 로고
    • Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1603. Halbritter, G.; Knoch, F.; Wolski, A.; Kish, H. J. Organomet. Chem. 1995, 492, 87. Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. Westernacher, S.; Kisch, H. Monatsh. Chem. 1996, 127, 469.
    • (1996) Monatsh. Chem. , vol.127 , pp. 469
    • Westernacher, S.1    Kisch, H.2
  • 60
    • 1542789337 scopus 로고
    • The ruthenium-catalyzed conversion of vinylsilanes to ethylene and disilylethylene is known. Wakatuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703. Marciniec, B.; Pietraszuk, C. J. Organomet. Chem. 1991, 412, C1. See also Seki, Y.; Takeshita, K.; Kawamoto, K. J. Organomet. Chem. 1989, 369, 117.
    • (1991) J. Chem. Soc., Chem. Commun. , vol.703
    • Wakatuki, Y.1    Yamazaki, H.2    Nakano, M.3    Yamamoto, Y.4
  • 61
    • 0001812750 scopus 로고
    • The ruthenium-catalyzed conversion of vinylsilanes to ethylene and disilylethylene is known. Wakatuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703. Marciniec, B.; Pietraszuk, C. J. Organomet. Chem. 1991, 412, C1. See also Seki, Y.; Takeshita, K.; Kawamoto, K. J. Organomet. Chem. 1989, 369, 117.
    • (1991) J. Organomet. Chem. , vol.412
    • Marciniec, B.1    Pietraszuk, C.2
  • 62
    • 0001442962 scopus 로고
    • The ruthenium-catalyzed conversion of vinylsilanes to ethylene and disilylethylene is known. Wakatuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703. Marciniec, B.; Pietraszuk, C. J. Organomet. Chem. 1991, 412, C1. See also Seki, Y.; Takeshita, K.; Kawamoto, K. J. Organomet. Chem. 1989, 369, 117.
    • (1989) J. Organomet. Chem. , vol.369 , pp. 117
    • Seki, Y.1    Takeshita, K.2    Kawamoto, K.3
  • 65
    • 33847086579 scopus 로고
    • Casey, C. P.; Scheck, D. M. J. Am. Chem. Soc. 1980, 102, 2723. Casey, C. P.; Scheck, D. M. J. Am. Chem. Soc. 1980, 102, 2728.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2723
    • Casey, C.P.1    Scheck, D.M.2
  • 66
    • 0348002547 scopus 로고
    • Casey, C. P.; Scheck, D. M. J. Am. Chem. Soc. 1980, 102, 2723. Casey, C. P.; Scheck, D. M. J. Am. Chem. Soc. 1980, 102, 2728.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2728
    • Casey, C.P.1    Scheck, D.M.2
  • 67
    • 1542684075 scopus 로고    scopus 로고
    • note
    • GC analysis of the crude reaction mixture indicated that they were formed in a ratio of 21:1.
  • 68
    • 85086290288 scopus 로고    scopus 로고
    • note
    • 3 resulted in formation of C-C bond at 1-position (refs 18a and e). The difference between the two reactions in regioselectivity may suggest the difference in the mechanism of C-C bond-forming step. This will be discussed in the future paper.
  • 70
    • 0020833988 scopus 로고
    • Yamazaki, H.; Wakatsuki, Y. J. Organomet. Chem. 1978, 149, 377. Yamazaki, H.; Hong, P. J. Mol. Catal. 1983, 21, 133.
    • (1983) J. Mol. Catal. , vol.21 , pp. 133
    • Yamazaki, H.1    Hong, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.