메뉴 건너뛰기




Volumn , Issue 9, 2001, Pages 918-919

Mechanistic study of the Ru(H)2(CO)(PPh3)3-catalyzed addition of C-H bonds in aromatic esters to olefins

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0035540115     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.918     Document Type: Article
Times cited : (67)

References (33)
  • 7
    • 0000782830 scopus 로고    scopus 로고
    • For examples, see: Y. Guari, S. Sabo-Etienne, and B. Chaudret, J. Am. Chem. Soc., 120, 4228 (1998); P. W. R. Harris, C. E. F. Rickard, and P. D. Woodgate, J. Organomet. Chem., 601, 172 (2000).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4228
    • Guari, Y.1    Sabo-Etienne, S.2    Chaudret, B.3
  • 9
    • 0032501467 scopus 로고    scopus 로고
    • 3-catalyzed C-H/olefin coupling, see: T. Matsubara, N. Koga, D. G. Musaev, and K. Morokuma, J. Am. Chem. Soc., 120, 12692 (1998); T. Matsubara, N. Koga, D. G. Musaev, and K. Morokuma, Organometallics, 19, 2318 (2000).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 12692
    • Matsubara, T.1    Koga, N.2    Musaev, D.G.3    Morokuma, K.4
  • 10
    • 0033703742 scopus 로고    scopus 로고
    • 3-catalyzed C-H/olefin coupling, see: T. Matsubara, N. Koga, D. G. Musaev, and K. Morokuma, J. Am. Chem. Soc., 120, 12692 (1998); T. Matsubara, N. Koga, D. G. Musaev, and K. Morokuma, Organometallics, 19, 2318 (2000).
    • (2000) Organometallics , vol.19 , pp. 2318
    • Matsubara, T.1    Koga, N.2    Musaev, D.G.3    Morokuma, K.4
  • 11
    • 0000997549 scopus 로고
    • For the reaction mechanism of rhodium-catalyzed carbonylation of arenes, see: T. Sakakura, T. Sodeyama, K. Sasaki, K. Wada, and M. Tanaka, J. Am. Chem. Soc., 112, 7221 (1990); S. E. Boyd, L. D. Field, and M. G. Partridge, J. Am. Chem. Soc., 116, 9492 (1994); G. P. Rosini, W. T. Boese, and A. S. Goldman, J. Am. Chem. Soc., 116, 9498 (1994); J. S. Bridgewater, B. Lee, S. Bernhard, J. R. Schoonover, and P. C. Ford, Organometallics, 16, 5592 (1997).
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7221
    • Sakakura, T.1    Sodeyama, T.2    Sasaki, K.3    Wada, K.4    Tanaka, M.5
  • 12
    • 0000028982 scopus 로고
    • For the reaction mechanism of rhodium-catalyzed carbonylation of arenes, see: T. Sakakura, T. Sodeyama, K. Sasaki, K. Wada, and M. Tanaka, J. Am. Chem. Soc., 112, 7221 (1990); S. E. Boyd, L. D. Field, and M. G. Partridge, J. Am. Chem. Soc., 116, 9492 (1994); G. P. Rosini, W. T. Boese, and A. S. Goldman, J. Am. Chem. Soc., 116, 9498 (1994); J. S. Bridgewater, B. Lee, S. Bernhard, J. R. Schoonover, and P. C. Ford, Organometallics, 16, 5592 (1997).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9492
    • Boyd, S.E.1    Field, L.D.2    Partridge, M.G.3
  • 13
    • 0000042822 scopus 로고
    • For the reaction mechanism of rhodium-catalyzed carbonylation of arenes, see: T. Sakakura, T. Sodeyama, K. Sasaki, K. Wada, and M. Tanaka, J. Am. Chem. Soc., 112, 7221 (1990); S. E. Boyd, L. D. Field, and M. G. Partridge, J. Am. Chem. Soc., 116, 9492 (1994); G. P. Rosini, W. T. Boese, and A. S. Goldman, J. Am. Chem. Soc., 116, 9498 (1994); J. S. Bridgewater, B. Lee, S. Bernhard, J. R. Schoonover, and P. C. Ford, Organometallics, 16, 5592 (1997).
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9498
    • Rosini, G.P.1    Boese, W.T.2    Goldman, A.S.3
  • 14
    • 0000115045 scopus 로고    scopus 로고
    • For the reaction mechanism of rhodium-catalyzed carbonylation of arenes, see: T. Sakakura, T. Sodeyama, K. Sasaki, K. Wada, and M. Tanaka, J. Am. Chem. Soc., 112, 7221 (1990); S. E. Boyd, L. D. Field, and M. G. Partridge, J. Am. Chem. Soc., 116, 9492 (1994); G. P. Rosini, W. T. Boese, and A. S. Goldman, J. Am. Chem. Soc., 116, 9498 (1994); J. S. Bridgewater, B. Lee, S. Bernhard, J. R. Schoonover, and P. C. Ford, Organometallics, 16, 5592 (1997).
    • (1997) Organometallics , vol.16 , pp. 5592
    • Bridgewater, J.S.1    Lee, B.2    Bernhard, S.3    Schoonover, J.R.4    Ford, P.C.5
  • 15
    • 0000360319 scopus 로고    scopus 로고
    • For the reaction mechanism of the rhodium-catalyzed intramolecular hydroacylation of 4-pentenals, see: B. Bosnich, Acc. Chem. Res., 31, 667 (1998).
    • (1998) Acc. Chem. Res. , vol.31 , pp. 667
    • Bosnich, B.1
  • 16
    • 0003965863 scopus 로고
    • 71st ed., ed. by D. R. Lide, CRC Press, Boston
    • "Handbook of Chemistry and Physics," 71st ed., ed. by D. R. Lide, CRC Press, Boston (1990), pp 9-96.
    • (1990) Handbook of Chemistry and Physics , pp. 9-96
  • 18
    • 0007158587 scopus 로고    scopus 로고
    • note
    • 5 and three vinylic positions in 2) (Scheme 1), the hydrogen intensity should be 0.60 H (the theoretical value) at each position.
  • 19
    • 0007158588 scopus 로고    scopus 로고
    • note
    • Supporting information (3 pages) is available on request to the author by telefax (+81-6-6879-7396).
  • 20
    • 0007157567 scopus 로고    scopus 로고
    • note
    • 5 and triethylvinylsilane under reaction conditions similar to those shown in Scheme 1. This result indicates that the substituent on the silicon atom does not affect the rate-determining step.
  • 21
    • 0007157071 scopus 로고
    • ed. by C. L. Collins and N. S. Bowman, ACS Monograph, New York Chap. 6
    • A. Fry, in "Isotope Effects in Chemical Reactions," ed. by C. L. Collins and N. S. Bowman, ACS Monograph, New York (1970), Chap. 6; L. Melander and W. H. Saunders, Jr., in "Reaction Rates of Isotopic Molecules," John Wiley & Sons, Inc., New York (1980), Chap. 4.4.
    • (1970) Isotope Effects in Chemical Reactions
    • Fry, A.1
  • 22
    • 0004152918 scopus 로고
    • John Wiley & Sons, Inc., New York Chap. 4.4
    • A. Fry, in "Isotope Effects in Chemical Reactions," ed. by C. L. Collins and N. S. Bowman, ACS Monograph, New York (1970), Chap. 6; L. Melander and W. H. Saunders, Jr., in "Reaction Rates of Isotopic Molecules," John Wiley & Sons, Inc., New York (1980), Chap. 4.4.
    • (1980) Reaction Rates of Isotopic Molecules
    • Melander, L.1    Saunders W.H., Jr.2
  • 23
    • 0007289906 scopus 로고    scopus 로고
    • note
    • 14
  • 24
    • 0000939121 scopus 로고
    • For representative reports, see: D. A. Singleton and A. A. Thomas, J. Am. Chem. Soc., 117, 9357 (1995); D. A. Singleton, S. R. Merrigan, B. J. Kim, P. Beak, L. M. Phillips, and J. K. Lee, J. Am. Chem. Soc., 122, 3296 (2000).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9357
    • Singleton, D.A.1    Thomas, A.A.2
  • 27
    • 0007298980 scopus 로고    scopus 로고
    • note
    • 3) was carried out, H/D scrambling was observed. From this observation, we believe that the C-C bond formation step is also rate-determining.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.