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Volumn 126, Issue 33, 2004, Pages 10331-10338

Ni-catalyzed, ZnCl2-assisted domino coupling of enones, alkynes, and alkenes

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COUPLED CIRCUITS; HYDROGEN; NICKEL COMPOUNDS; OXIDATION;

EID: 4143074756     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047580a     Document Type: Article
Times cited : (29)

References (57)
  • 3
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    • Dauben, W. G., Ed.; Wiley: New York
    • Reviews: (a) Heck, R. F. In Organic Reactions; Dauben, W. G., Ed.; Wiley: New York, 1982; Vol. 27, p 345.
    • (1982) Organic Reactions , vol.27 , pp. 345
    • Heck, R.F.1
  • 5
    • 0000134380 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • (c) Söderberg, B. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 241.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 241
    • Söderberg, B.C.1
  • 11
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    • Overman, L. E., Ed.; Wiley: New York
    • (a) Link, J. T. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2003; Vol. 60, p 157.
    • (2003) Organic Reactions , vol.60 , pp. 157
    • Link, J.T.1
  • 36
    • 0035809288 scopus 로고    scopus 로고
    • For related works of the nickel-promoted domino reaction, Montgomery recently reported generation and characterization of the O-bound nickel enolate. See: (b) Amarasinghe, K. K. D.; Chowdhury, S. K.; Heeg, M. J.; Montgomery, J. Organometallics 2001, 20, 370.
    • (2001) Organometallics , vol.20 , pp. 370
    • Amarasinghe, K.K.D.1    Chowdhury, S.K.2    Heeg, M.J.3    Montgomery, J.4
  • 37
    • 0242330786 scopus 로고    scopus 로고
    • (c) Mahandru, G. M.; Skauge, A. R. L.; Chowdhury, S. K.; Amarasinghe, K. K. D.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 2003, 125, 13481. The O-enolate, which is generated by the oxidative cyclization of an enal and alkyne with Ni (O) species, contains a cis double bond in a seven-membered ring. However, a metalacycle generated by a cyclic enone such as 2-cyclopenten-1-one and alkyne with Ni (O) would not be the corresponding O-enolate, because the enolate contains a strained trans double bond in the seven-membered ring.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13481
    • Mahandru, G.M.1    Skauge, A.R.L.2    Chowdhury, S.K.3    Amarasinghe, K.K.D.4    Heeg, M.J.5    Montgomery, J.6
  • 39
  • 41
    • 4143063762 scopus 로고    scopus 로고
    • note
    • 3N was added in the absence of zinc dust, the Ni-catalyzed reaction did not proceed. In contrast, in the Pd-catalyzed Mizoroki-Heck reaction, it is well-known that a variety of bases promote the regeneration of Pd(0) from H-Pd-X species generated by β-hydrogen elimination. See refs 1-3.
  • 43
    • 0001150096 scopus 로고
    • For the β-carbon vs β-hydrogen elimination of 7 and 8, Miller and co-workers reported that the nickel-catalyzed skeletal rearrangement of i to iv was consistent with a mechanism that involved the β-carbon elimination of a complex iii induced by the cyclopropanation of ii.12a However, product v derived from the β-hydrogen elimination of iii was not obtained. On the other hand, they also reported that the same nickel complex catalyzed the rearrangement of v to iv.12b This result suggests that a rapid equilibrium is present between iii and v. In a similar manner, the presence of rapid equilibrium between 7 (or 8) and 10 (and/or 11) cannot be ruled out. (a) Pinke, P. A.; Miller, R. G. J. Am. Chem. Soc. 1974, 96, 4221.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 4221
    • Pinke, P.A.1    Miller, R.G.2
  • 45
    • 0000938189 scopus 로고
    • Whereas a half-life of 30 h at 27 °C and an activation energy of ca. 26 kcal/mol were characteristic of the equilibration of homoallyl Grignard reagent,13a the half-life for the nickel-catalyzed conversion of i to isomeric products such as iv was <2 min at 25 °C.13b (a) Howden, M. E. H.; Maerker, A.; Burdon, J.; Roberts, J. D. J. Am. Chem. Soc. 1966, 88, 1732.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 1732
    • Howden, M.E.H.1    Maerker, A.2    Burdon, J.3    Roberts, J.D.4
  • 48
    • 4143124587 scopus 로고    scopus 로고
    • note
    • The reaction took place at room temperature for 3 days and gave 26 in 12% yield along with some unidentified products.
  • 50
    • 0010736039 scopus 로고
    • For the Ni-catalyzed "Mizoroki-Heck"-type reaction, see: (a) Mori, M.; Ban, Y. Tetrahedron Lett. 1976, 1803.
    • (1976) Tetrahedron Lett. , pp. 1803
    • Mori, M.1    Ban, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.