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Volumn 7, Issue 23, 2005, Pages 5167-5170

Benzylic oxidation catalyzed by dirhodium(II,III) caprolactamate

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; FUSED HETEROCYCLIC RINGS; NAPHTHALENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PALMARUMYCIN CP2; RHODIUM; SPIRO COMPOUND;

EID: 28244482843     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0520020     Document Type: Article
Times cited : (203)

References (45)
  • 2
    • 0000481954 scopus 로고
    • Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford
    • (b) Mimoun, H. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, 1987; Vol. 6, p 317.
    • (1987) Comprehensive Coordination Chemistry , vol.6 , pp. 317
    • Mimoun, H.1
  • 29
    • 28244459426 scopus 로고    scopus 로고
    • note
    • Anhydrous TBHP in decane was used.
  • 30
    • 28244457354 scopus 로고    scopus 로고
    • note
    • In addition, catalyst decomposition was apparent after 1 h by a color change from dark red (indicative of a dirhodium(II,III) complex) to yellow/orange.
  • 33
    • 28244444109 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude reaction mixture prior to purification. Diphenylmethane (entry 6, Table 1) gave 57% conversion.
  • 34
    • 28244483126 scopus 로고    scopus 로고
    • note
    • Diones 3 and 5 are chromatographically stable but must be stored in a freezer to avoid decomposition.
  • 35
    • 0035963006 scopus 로고    scopus 로고
    • and references therein
    • Hodgetts, K. J. Tetrahedron Lett. 2001, 42, 3763 and references therein.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3763
    • Hodgetts, K.J.1
  • 36
    • 28244493407 scopus 로고    scopus 로고
    • note
    • Substrates containing a primary benzylic position, strong coordinating groups (e.g., pyridines or nitriles), or strong electron-withdrawing groups were unreactive under our protocol. The following substrates were examined and exemplify recalcitrant substrate classes: (Chemical Equation Presented)
  • 38
    • 28244472044 scopus 로고    scopus 로고
    • note
    • 3 did not convert 7 to 6.
  • 39
    • 28244475908 scopus 로고    scopus 로고
    • note
    • This experiment also demonstrates that catalytic activity can be restarted by simply applying additional oxidant.
  • 40
    • 0028480219 scopus 로고
    • The formation of ketones from mixed-peroxides with t-BuOOH under metal-catalyzed conditions has been reported: Muzart, J.; Ajjou, A. N. J. Mol. Catal. 1994, 92, 141. We thank the reviewer for bringing this to our attention.
    • (1994) J. Mol. Catal. , vol.92 , pp. 141
    • Muzart, J.1    Ajjou, A.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.