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Volumn 69, Issue 20, 2004, Pages 6761-6765

Neighboring group effect in Pd-catalyzed carbonylation terminated by lactonization: A need for a protective group and/or DMF

Author keywords

[No Author keywords available]

Indexed keywords

BUTENES; CHELATION; ESTERIFICATION; FUNGUS PROTECTION; PALLADIUM; SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 4644319586     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049114+     Document Type: Article
Times cited : (13)

References (30)
  • 7
    • 7044235861 scopus 로고    scopus 로고
    • (a) For a review, see: Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Sugihara, T.; Coperet, C.; Owczarczyk, Z.; Hairing, L. S.; Negishi, E.-i. J. Am. Chem. Soc. 1994, 116, 7923. (c) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1998, 576, 65.
    • (1996) Chem. Rev. , vol.96 , pp. 365
    • Negishi, E.-I.1    Copéret, C.2    Ma, S.3    Liou, S.-Y.4    Liu, F.5
  • 8
    • 0000219093 scopus 로고
    • (a) For a review, see: Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Sugihara, T.; Coperet, C.; Owczarczyk, Z.; Hairing, L. S.; Negishi, E.-i. J. Am. Chem. Soc. 1994, 116, 7923. (c) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1998, 576, 65.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7923
    • Sugihara, T.1    Coperet, C.2    Owczarczyk, Z.3    Hairing, L.S.4    Negishi, E.-I.5
  • 9
    • 0346543813 scopus 로고    scopus 로고
    • (a) For a review, see: Negishi, E.-i.; Copéret, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365. (b) Sugihara, T.; Coperet, C.; Owczarczyk, Z.; Hairing, L. S.; Negishi, E.-i. J. Am. Chem. Soc. 1994, 116, 7923. (c) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1998, 576, 65.
    • (1998) J. Organomet. Chem. , vol.576 , pp. 65
    • Grigg, R.1    Sridharan, V.2
  • 12
    • 0030603120 scopus 로고    scopus 로고
    • Treatment of (Z)-3-iodo-4-triphenylmethoxybut-2-en-1-ol with MsCl afforded the corresponding mesylate in 40% isolated yield; see: Copéret, C.; Ma, S.; Sugihara, T.; Negishi, E.-i. Tetrahedron 1996, 52, 11529.
    • (1996) Tetrahedron , vol.52 , pp. 11529
    • Copéret, C.1    Ma, S.2    Sugihara, T.3    Negishi, E.-I.4
  • 15
    • 4644322134 scopus 로고
    • DMF has been shown to be one of the most desirable solvents for Pd-catalyzed cross-coupling reactions (Negishi, E.-i.; Owczarczyk, Z.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4456) and has been frequently used in carbonylation reactions as well.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4456
    • Negishi, E.-I.1    Owczarczyk, Z.2    Swanson, D.R.3
  • 17
    • 4644363960 scopus 로고    scopus 로고
    • See the literature in ref 6
    • See the literature in ref 6.
  • 18
    • 4644270788 scopus 로고    scopus 로고
    • note
    • In MeOH as the solvent (53% yield), the rest was recovered starting material.
  • 19
    • 0344823680 scopus 로고    scopus 로고
    • For the most recent results supporting this view, see also: Kadnikov, D. V.; Larock, R. C. J. Org. Chem. 2003, 68, 9423.
    • (2003) J. Org. Chem. , vol.68 , pp. 9423
    • Kadnikov, D.V.1    Larock, R.C.2
  • 22
    • 0034917285 scopus 로고    scopus 로고
    • In this case, the initially formed alkenylpalladium intermediate could have been stabilized by the chelation of the carbonyl oxygen to Pd, even though it should be noted that a seven-membered chelate ring would thus be formed. This kind of stabilizing effect has been proposed by Maleczka et al. to explain the regioselectivity of Pd-mediated hydrostannations of terminal alkynes; see: Rice, B. M.; Whitehead, S. L.; Horvath, C. M.; Muchnij, J. A.; Maleczka, R. E., Jr. Synthesis 2001, 1495.
    • (2001) Synthesis , pp. 1495
    • Rice, B.M.1    Whitehead, S.L.2    Horvath, C.M.3    Muchnij, J.A.4    Maleczka Jr., R.E.5
  • 25
    • 4644364220 scopus 로고    scopus 로고
    • See ref 17a
    • (a) See ref 17a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.