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Volumn 63, Issue 26, 1998, Pages 9608-9609

Palladium catalyzed alkylation with allylic acetates under neutral conditions

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALLYL COMPOUND; PALLADIUM;

EID: 0032567371     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981599c     Document Type: Article
Times cited : (59)

References (29)
  • 1
    • 0001796593 scopus 로고
    • Schlösser, M., Ed.; Wiley: New York, Chapter 5
    • (a) Hegedus L. S. In Organometallics in Synthesis; Schlösser, M., Ed.; Wiley: New York, 1994; Chapter 5, pp 385-459.
    • (1994) Organometallics in Synthesis , pp. 385-459
    • Hegedus, L.S.1
  • 5
    • 0001737038 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, Chapter 8.2
    • (e) Harrington P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, Chapter 8.2, pp 798-903.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 798-903
    • Harrington, P.J.1
  • 9
    • 0000492007 scopus 로고
    • To the best of our knowledge, we could find only two nonrationalized precedents of Pd(0)-catalyzed allylic alkylations using allylic acetates in the absence of bases, (a)
    • To the best of our knowledge, we could find only two nonrationalized precedents of Pd(0)-catalyzed allylic alkylations using allylic acetates in the absence of bases, (a) Moreno-Manas, M.; Prat, M.; Ribas, J.; Virgili, A. Tetrahedron Lett. 1988,29, 581.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 581
    • Moreno-Manas, M.1    Prat, M.2    Ribas, J.3    Virgili, A.4
  • 11
    • 0344887064 scopus 로고
    • Ethyl nitroacetate
    • Sources of the pK, values reported in Table 1. (Phenylsulfonyl)nitromethane, barbituric acid, malononitrile, Meldrum's acid, bis(phenylsulfonyDmethane, ethyl acetoacetate, diethyl malonate: (a) Bordwell, F. G. Ace. Chem. Res. 1988, 21, 456. Ethyl nitroacetate:
    • (1988) Ace. Chem. Res. , vol.21 , pp. 456
    • Bordwell, F.G.1
  • 13
    • 3543021019 scopus 로고
    • The pK, values of methyl phenylsulfonyl acetate and of ethyl nitroacetate in DMSO have been estimated.
    • Pearson, R. G.; Dillon, R. L. J. Am. Chem. Soc. 1953, 75, 2439. The pK, values of methyl phenylsulfonyl acetate and of ethyl nitroacetate in DMSO have been estimated.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 2439
    • Pearson, R.G.1    Dillon, R.L.2
  • 18
    • 0000016787 scopus 로고    scopus 로고
    • In a recent example of palladium-catalyzed C-Mitsunobu condensation a similar palladium complex has been postulated
    • In a recent example of palladium-catalyzed C-Mitsunobu condensation a similar palladium complex has been postulated: Shing, T. K M.; Li, L.-H.; Narkunan K. J. Org. Chem. 1997, 62, 1617.
    • (1997) J. Org. Chem. , vol.62 , pp. 1617
    • Shing, T.K.M.1    Li, L.-H.2    Narkunan, K.3
  • 19
    • 0004143671 scopus 로고
    • Such a coordination is also expected to synergistically enhance the acidity of the Pd(II)-coordinated active méthylènes, (a) VCH: Weinheim
    • Such a coordination is also expected to synergistically enhance the acidity of the Pd(II)-coordinated active méthylènes, (a) Constable, E. C. Metals'and Ligand Reactivity; VCH: Weinheim, 1995.
    • (1995) Metals'and Ligand Reactivity
    • Constable, E.C.1
  • 21
    • 33847510992 scopus 로고    scopus 로고
    • At present, an alternative path involving the transient formation of a σ-allyl Pd complex maintaining two trans-disposed phophines cannot be ruled out.
    • At present, an alternative path involving the transient formation of a σ-allyl Pd complex maintaining two trans-disposed phophines cannot be ruled out.
  • 23
    • 33847511197 scopus 로고    scopus 로고
    • The pK. values of HC1 and AcOH in DMSO are 1.8 and 12.3, respectively. See ref lOa.
    • The pK. values of HC1 and AcOH in DMSO are 1.8 and 12.3, respectively. See ref lOa.
  • 24
    • 0023850740 scopus 로고
    • For reported examples of Pd-catalyzed allylic alkylations of active méthylènes in the presence of bases, or using already deprotonated nucleophiles, see, for example: (a)
    • For reported examples of Pd-catalyzed allylic alkylations of active méthylènes in the presence of bases, or using already deprotonated nucleophiles, see, for example: (a) Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 770,621.
    • (1988) J. Am. Chem. Soc. , vol.770 , pp. 621
    • Trost, B.M.1    Kuo, G.H.2    Benneche, T.3
  • 29
    • 0000903824 scopus 로고
    • A related Pd(0)-catalyzed condensation between active méthylènes ' and aliènes under neutral conditions has been recently reported. In that case, the mechanism has been rationalized on the basis of the initial oxidative addition of Pd(0) into the C-H bond of the active méthylène followed by carbopalladation.
    • A related Pd(0)-catalyzed condensation between active méthylènes ' and aliènes under neutral conditions has been recently reported. (Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 776, 6019). In that case, the mechanism has been rationalized on the basis of the initial oxidative addition of Pd(0) into the C-H bond of the active méthylène followed by carbopalladation.
    • (1994) J. Am. Chem. Soc. , vol.776 , pp. 6019
    • Yamamoto, Y.1    Al-Masum, M.2    Asao, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.