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Volumn 46, Issue 14, 2007, Pages 2531-2534

Acylation of electrophilic olefins through decatungstate-photocatalyzed activation of aldehydes

Author keywords

Acylation; Aldehydes; Alkenes; Photochemistry; Radical reactions

Indexed keywords

ACYLATION; ALDEHYDES; KETONES; LOW TEMPERATURE EFFECTS; PHOTOCATALYSIS;

EID: 34250812663     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604820     Document Type: Article
Times cited : (177)

References (38)
  • 13
    • 0037429034 scopus 로고    scopus 로고
    • For recent examples on the hydrogen-abstraction properties of excited aromatic ketones, see: a
    • For recent examples on the hydrogen-abstraction properties of excited aromatic ketones, see: a) D. Dondi, I. Caprioli, M. Fagnoni, M. Mella, A. Albini, Tetrahedron 2003, 59, 947-957;
    • (2003) Tetrahedron , vol.59 , pp. 947-957
    • Dondi, D.1    Caprioli, I.2    Fagnoni, M.3    Mella, M.4    Albini, A.5
  • 26
    • 34250816571 scopus 로고    scopus 로고
    • Note that the acylation was successful with ketones 2c,d,f despite their competitive absorption; compare with Ref. [11b].
    • Note that the acylation was successful with ketones 2c,d,f despite their competitive absorption; compare with Ref. [11b].
  • 33
    • 0000884797 scopus 로고    scopus 로고
    • For a related example of photochemical acylation reaction at temperatures below ambient temperatures, see: P. Gottschalk, D. C. Neckers, J. Org. Chem. 1985, 50, 3498-3502
    • For a related example of photochemical acylation reaction at temperatures below ambient temperatures, see: P. Gottschalk, D. C. Neckers, J. Org. Chem. 1985, 50, 3498-3502.
  • 34
    • 34250851069 scopus 로고    scopus 로고
    • -1; see Ref. [1].
    • -1; see Ref. [1].
  • 35
    • 34250871331 scopus 로고    scopus 로고
    • -1). See Ref. [18a].
    • -1). See Ref. [18a].
  • 36
    • 34250837169 scopus 로고    scopus 로고
    • The rate constants for the decarbonylation of aldehydes and for the addition of pivaloyl radical to acrylonitrile are known with considerable uncertainty, In the hypothesis that these values roughly apply to the present reaction, the acylation/alkylation ratios are predicted to be 3.5 and 0.9 for secondary and tertiary aldehydes at 23°C, and 0.005 and 0.02 at -20°C. This prediction fits with the observed trend, although the k -CO/kadd ratio is clearly larger in the present reactions, particularly for tertiary aldehydes
    • add ratio is clearly larger in the present reactions, particularly for tertiary aldehydes.
  • 37
    • 0004775241 scopus 로고    scopus 로고
    • Some exceptions are known, but these involve either a highly activated trap such as a captodative olefin (S. Mignani, R. Merenyi, Z. Janousek, H. G. Viehe, Bull. Soc. Chim. Belg. 1984, 93, 991-997)
    • Some exceptions are known, but these involve either a highly activated trap such as a captodative olefin (S. Mignani, R. Merenyi, Z. Janousek, H. G. Viehe, Bull. Soc. Chim. Belg. 1984, 93, 991-997)
  • 38
    • 0001397899 scopus 로고    scopus 로고
    • or reactions on a metal center rather than via the free radical in solution, as when starting from alkyliron carbonyls (B. Giese, G. Thoma, Helv. Chim. Acta 1991, 74, 1143-1155).
    • or reactions on a metal center rather than via the free radical in solution, as when starting from alkyliron carbonyls (B. Giese, G. Thoma, Helv. Chim. Acta 1991, 74, 1143-1155).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.