메뉴 건너뛰기




Volumn 45, Issue 41, 2006, Pages 6914-6917

PdII-catalyzed aerobic allylic oxidative carbocyclization of allene-substituted olefins: Immobilization of an oxygen-activating catalyst

Author keywords

Aerobic oxidation; Allenes; Allylic oxidation; Homogeneous catalysis; Palladium

Indexed keywords

CATALYSIS; CATALYSTS; ELECTRON TRANSITIONS; OXIDATION; PALLADIUM;

EID: 33750438437     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602421     Document Type: Article
Times cited : (94)

References (47)
  • 2
    • 0003678023 scopus 로고
    • American Chemical Society, Washington, DC, (ACS Monograph Ser. 186)
    • b) M. Hudlicky, Oxidations in Organic Chemistry, American Chemical Society, Washington, DC, 1990 (ACS Monograph Ser. 186);
    • (1990) Oxidations in Organic Chemistry
    • Hudlicky, M.1
  • 22
    • 0942287138 scopus 로고    scopus 로고
    • and references therein
    • D. V. Deubel, J. Am. Chem. Soc. 2004, 126, 996, and references therein.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 996
    • Deubel, D.V.1
  • 24
    • 4143153074 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2004, 43, 3400, and references therein.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3400
  • 36
    • 33644760299 scopus 로고    scopus 로고
    • For a recent interesting anaerobic oxidation with C-C bond formation through an outer-sphere nucleophilic attack of indole on an (olefin)palladium complex, see: C. Liu, R. A. Widenhoefer, Chem. Eur. J. 2006, 12, 2371.
    • (2006) Chem. Eur. J. , vol.12 , pp. 2371
    • Liu, C.1    Widenhoefer, R.A.2
  • 39
    • 33750470896 scopus 로고    scopus 로고
    • note
    • The acyclic starting materials 1g-h were obtained in the same way as the cyclic starting materials 1a-e from the corresponding acyclic allylic acetates.
  • 41
    • 33750450630 scopus 로고    scopus 로고
    • note
    • 2 atmosphere, a mixture of 2a, 6, 7, and additional unidentified by-products were formed; unfortunately the ratio between 2a, 6, and 7 could not be determined.
  • 42
    • 33750452787 scopus 로고    scopus 로고
    • note
    • A similar isomerization occurs in the palladium(0)-catalyzed cycloisomerization reaction of enallenes. See Ref. [18].
  • 43
    • 33646449394 scopus 로고    scopus 로고
    • The FePc was attached to a polystyrene resin (aminomethylated polystyrene (50-100 mesh)) through a sulfonamide group; for reviews on solid-phase reactions, see: a) B. A. Lorsbach, M. Kurth, Chem. Rev. 1999, 99, 1549;
    • (1999) Chem. Rev. , vol.99 , pp. 1549
    • Lorsbach, B.A.1    Kurth, M.2
  • 45
    • 33750457434 scopus 로고    scopus 로고
    • note
    • These results are consistent with the rate-determining step being the reoxidation of the hydroquinone to its corresponding quinone.
  • 46
    • 0001532766 scopus 로고
    • Further studies on the mechanism of the reoxidation of palladium by the quinone species are in development and will be presented in a future paper; for information about the previously described mechanism, see, for example: a) H. Grennberg, A. Gogoll, J.-E. Bäckvall, Organometallics 1993, 12, 1790;
    • (1993) Organometallics , vol.12 , pp. 1790
    • Grennberg, H.1    Gogoll, A.2    Bäckvall, J.-E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.