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Volumn 128, Issue 1, 2006, Pages 202-209

Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation: Synthesis of phthalimidine and indene derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CARBON; CATALYSTS; CHEMICAL BONDS; DERIVATIVES; RHENIUM; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

EID: 30844466406     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054216i     Document Type: Article
Times cited : (258)

References (70)
  • 26
    • 8644263966 scopus 로고    scopus 로고
    • and references therein
    • For the building blocks for medicines, see: Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 13, 2397 and references therein.
    • (2004) Synlett , vol.13 , pp. 2397
    • Korte, A.1    Legros, J.2    Bolm, C.3
  • 31
    • 0002043236 scopus 로고
    • Phthalimidine (isoindolinone, benzo-γ-lactam) has a five-membered ring with one nitrogen atom and is a part of the structure of bioactive compounds: (a) Fajardo, V.; Elango, V.; Cassels, B. K.; Shamma, M. Tetrahedron Lett. 1982, 23, 39.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 39
    • Fajardo, V.1    Elango, V.2    Cassels, B.K.3    Shamma, M.4
  • 40
    • 30844443383 scopus 로고    scopus 로고
    • note
    • 1H NMR yields were determined by using 1,1,2,2-tetrachloroethane as an internal standard.
  • 41
    • 30844459812 scopus 로고    scopus 로고
    • note
    • Heat and/or a rhenium catalyst promote interconversion of substituents at 1,2-position of the indene framework. The elucidation of the mechanism is now under consideration.
  • 43
    • 6044253710 scopus 로고    scopus 로고
    • There is another possible pathway: C-H bond activation is reversible and can occur at all positions on the aromatic ring. After C-H bond activation, the coordinating group acts to trap the ortho-C-H bond addition product and stable chelated intermediate. See: Zhang, X.; Kanzelberger, M.; Emge, T. J.; Goldman, A. S. J. Am. Chem. Soc. 2004, 126, 13192.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13192
    • Zhang, X.1    Kanzelberger, M.2    Emge, T.J.3    Goldman, A.S.4
  • 46
    • 30844460915 scopus 로고    scopus 로고
    • note
    • 2 with aldimine, we could not observe the formation of the intermediate.
  • 47
    • 30844446825 scopus 로고    scopus 로고
    • note
    • 1H NMR yields of 6 were determined based on dibromomethane as an internal standard.
  • 48
    • 30844438422 scopus 로고    scopus 로고
    • note
    • 5 did not promote the formation reaction of 6a.
  • 49
    • 30844439769 scopus 로고    scopus 로고
    • note
    • Under reflux conditions, 6a was obtained irregularly as time passed. That is, yields of 6a were 3% (1 h), 18% (3 h), 95% (8 h), and >99% (24 h), respectively. These results indicate the existence of an induction time to form active species to catalyze the formation reaction of phthalimidine derivatives. However, the structure of the active species is still not clear.
  • 50
    • 30844439050 scopus 로고    scopus 로고
    • note
    • 2 in 1,2-dichloroethane in quantitative yield under reflux conditions, the yield decreased to 27% at 70 °C, and the reaction did not proceed at all at 50 °C.
  • 51
    • 0027913099 scopus 로고
    • In the following reports, compounds derived from double C-H bond activation and insertion of unsaturated molecules at two ortho-positions were obtained as side products: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529.
    • (1993) Nature , vol.366 , pp. 529
    • Murai, S.1    Kakiuchi, F.2    Sekine, S.3    Tanaka, Y.4    Kamatani, A.5    Sonoda, M.6    Chatani, N.7
  • 57
    • 30844455251 scopus 로고    scopus 로고
    • note
    • 2 under reflux conditions, 2-phenylethylisocyanate was recovered quantitatively. Though this result shows that the problems are not in the stability of alkyl isocyanate, the reason is not clear.
  • 58
    • 30844456303 scopus 로고    scopus 로고
    • note
    • The reactivities of aldimines bearing an electron-donating or an electron-withdrawing group toward acetylenes or isocyanates are opposite. The reason for these results is not clear yet.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.