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Volumn 52, Issue 17, 2011, Pages 2172-2175

Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; ALKYNYL GROUP; HALIDE; NICKEL COMPLEX; ZIRCONOCENE;

EID: 79953221425     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.124     Document Type: Article
Times cited : (17)

References (34)
  • 1
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    • For the discovery of Ni/Cr-mediated coupling reactions, see: (a)
    • For the discovery of Ni/Cr-mediated coupling reactions, see: (a) Jin, H.; Uenishi, J.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644;
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 5644
    • Jin, H.1    Uenishi, J.2    Christ, W.J.3    Kishi, Y.4
  • 3
    • 28844477490 scopus 로고    scopus 로고
    • For cataytic non-asymmetric Cr-mediated coupling reactions, see: (a)
    • For cataytic non-asymmetric Cr-mediated coupling reactions, see: (a) Namba, K.; Wang, J.; Cui, S.; Kishi, Y. Org. Lett. 2005, 7, 5421;
    • (2005) Org. Lett. , vol.7 , pp. 5421
    • Namba, K.1    Wang, J.2    Cui, S.3    Kishi, Y.4
  • 9
    • 79953172299 scopus 로고    scopus 로고
    • For preparation of Ni-catalysts, see Ref. 2
    • For preparation of Ni-catalysts, see Ref. 2.
  • 10
    • 79953205279 scopus 로고    scopus 로고
    • For abbreviation of ligands, see Figure 2
    • For abbreviation of ligands, see Figure 2.
  • 11
    • 79953183707 scopus 로고    scopus 로고
    • note
    • 2 reaches the saturation at 4 mol %.
  • 12
    • 79953171226 scopus 로고    scopus 로고
    • note
    • 3).
  • 13
    • 79953173655 scopus 로고    scopus 로고
    • note
    • 2, the homocoupling of 2-bromopyridine gave approximately 50% conversion for 2 days at room temperature.
  • 14
    • 85065137145 scopus 로고
    • In addition to the classical Ullmann procedure, dipyridyls are prepared via homocoupling of the corresponding halopyridines in the presence of copper, palladium, or nickel complexes. For selected examples, see: Cu-catalyst: (a)
    • In addition to the classical Ullmann procedure, dipyridyls are prepared via homocoupling of the corresponding halopyridines in the presence of copper, palladium, or nickel complexes. For selected examples, see: Cu-catalyst: (a) Fanta, P. E. Synthesis 1974, 9;
    • (1974) Synthesis , pp. 9
    • Fanta, P.E.1
  • 17
    • 79953211955 scopus 로고    scopus 로고
    • The coupling was not significantly improved by the use of 3-iodopyridine at room temperature
    • The coupling was not significantly improved by the use of 3-iodopyridine at room temperature.
  • 18
    • 79953202928 scopus 로고    scopus 로고
    • note
    • 2a However, we were limited in testing a wide range of dipyridyls, because of difficult access to certain dipyridyls.
  • 19
    • 79953174016 scopus 로고    scopus 로고
    • note
    • 2, (E)-1-iodohex-1-ene, (E)-2-iodohex-2-ene, (Z)-1-iodohex-1-ene, and (Z)-2-iodohex-2-ene gave the diene composing of 2.3:1 (E,E):(E,Z), 1.5:1 (E,E):(E,Z), 1:1 (E,E):(E,Z), and 1:5 (E,E):(E,Z), respectively.
  • 23
    • 33845374546 scopus 로고
    • Colon and Amatore proposed the mechanisms also involving Ni(I) and Ni(II) species as the intermediates
    • Colon and Amatore proposed the mechanisms also involving Ni(I) and Ni(II) species as the intermediates (Colon, I.; Kelsey, D. R. J. Org. Chem. 1986, 51, 2627;
    • (1986) J. Org. Chem. , vol.51 , pp. 2627
    • Colon, I.1    Kelsey, D.R.2
  • 25
    • 79953191532 scopus 로고    scopus 로고
    • note
    • 2 is a powerful activator for the Pd- or Ni-catalyzed cross-coupling reactions; for example, see Ref. 18.
  • 29
    • 0000175578 scopus 로고
    • For the related work from Negishi, see
    • For the related work from Negishi, see: Kondakov, D. Y.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 10771;
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10771
    • Kondakov, D.Y.1    Negishi, E.2
  • 33
    • 79953228122 scopus 로고    scopus 로고
    • 2, might be involved in the transmetallation
    • 2, might be involved in the transmetallation.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.