메뉴 건너뛰기




Volumn 69, Issue 16, 2004, Pages 5505-5508

A new, efficient method for direct α-alkenylation of β-dicarbonyl compounds and phenols using alkenyltriarylbismuthonium salts

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CARBON; ESTERS; ORGANIC COMPOUNDS; SALTS;

EID: 3543047971     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0492721     Document Type: Article
Times cited : (24)

References (35)
  • 2
    • 0000585779 scopus 로고
    • Transition metal-catalyzed direct α-alkenylation with haloalkenes, see: (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4833
    • Millard, A.A.1    Rathke, M.W.2
  • 16
    • 0033722982 scopus 로고    scopus 로고
    • The leaving ability of the triphenylbismuthonio group is higher than that of triflate ion. See: Matano, Y. Organometallics 2000, 19, 2258.
    • (2000) Organometallics , vol.19 , pp. 2258
    • Matano, Y.1
  • 22
    • 0347545735 scopus 로고
    • For reviews on the nucleophilic vinylic substitutions, see: (a) Rappoport, Z. Acc. Chem. Res. 1992, 25, 474.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 474
    • Rappoport, Z.1
  • 25
    • 3543034911 scopus 로고    scopus 로고
    • note
    • N1 mechanism, the stereochemistry of the vinylic moiety is inverted or lost significantly.
  • 26
    • 3543040333 scopus 로고
    • Zabicky, J. Ed.; Wiley: London, Chapter 2
    • Richey, H. G., Jr. In The Chemistry of Alkenes; Zabicky, J. Ed.; Wiley: London, 1970; Vol. 2, Chapter 2, pp 39-114.
    • (1970) The Chemistry of Alkenes , vol.2 , pp. 39-114
    • Richey, H.G.1
  • 27
    • 33947094631 scopus 로고
    • For a review, see: Stang, P. J. Chem. Rev. 1978, 78, 383.
    • (1978) J. Chem. Rev. , vol.78 , pp. 383
    • Stang, P.1
  • 28
    • 3543040976 scopus 로고    scopus 로고
    • note
    • If the reaction proceeds via the C-H insertion of a free alkylidene carbene, the E/Z ratio of 17e should be the same as that of 17e′.
  • 34
    • 3543031342 scopus 로고    scopus 로고
    • note
    • A similar ligand coupling mechanism was proposed by Barton and co-workers for the α-phenylation of enolizable substrates with tetraphenylbismuthonium salts. See ref 7.
  • 35
    • 33748667285 scopus 로고    scopus 로고
    • See also ref 6
    • X-ray crystallographic analyses of bismuthonium salts bearing o-anisyl groups disclosed the intramolecular coordination between the o-methoxy oxygens and the bismuth center. Suzuki, H.; Ikegami, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1997, 1609. See also ref 6.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 1609
    • Suzuki, H.1    Ikegami, T.2    Azuma, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.