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Volumn 69, Issue 10, 2004, Pages 3569-3571

Transition-Metal-Catalyzed Aldehydic C-H Activation by Azodicarboxylates

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ALDEHYDES; CATALYSIS; CHEMICAL BONDS; NITROGEN COMPOUNDS;

EID: 2442565557     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035456o     Document Type: Article
Times cited : (47)

References (35)
  • 12
    • 85050328347 scopus 로고
    • In related reactions, alcohols can be oxidized to the corresponding aldehydes and ketones; see: (j) Yoneda, F.; Suzuki, K.; Nitta, Y. J. Am. Chem. Soc. 1966, 88, 2328.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2328
    • Yoneda, F.1    Suzuki, K.2    Nitta, Y.3
  • 24
    • 2442554722 scopus 로고    scopus 로고
    • note
    • Although it is known that Lewis acids catalyze the ene-type reaction in "path c", catalyzed reactions have not been reported in "path d".
  • 25
    • 2442487530 scopus 로고    scopus 로고
    • note
    • 2.
  • 26
    • 2442615748 scopus 로고    scopus 로고
    • note
    • The reaction of substrates having slow conversion rate provides varying amounts of the corresponding hydrazodicarboxylate. (entries n, o) than that of the parent benzaldehyde (entry m). In case of 4-dimethylamino benzaldehyde (entry 1),
  • 27
    • 2442483454 scopus 로고    scopus 로고
    • note
    • The dependency of the extent of inhibition on the amount of the radical scavenger used in the reaction was pointed out by a reviewer.
  • 28
    • 2442584244 scopus 로고    scopus 로고
    • note
    • Duplicates of both the uncatalyzed and catalyzed reactions were run at 0, 1.0, 2.5, 5.0, and 10 mol % of the scavenger, 4,4′ -dithiobis-(2,6-di-tert-butylphenol), neat and in 0.2 M solution in EtOAc. The progression of the reaction was monitored by 1H NMR spectroscopy. The details of this experiment are described in the Supporting Information.
  • 35
    • 2442465523 scopus 로고    scopus 로고
    • note
    • The intramolecular trapping experiments of 5-hexenoyl radical derived from 5-hexenal and azodicarboxylate both with and without catalyst were also carried out. In both cases, the formation of 2-methyl cyclopentanone derivative was not observed; instead, only the normal coupled product (7b/7b′) was isolated in good yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.