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Volumn 127, Issue 14, 2005, Pages 5030-5031

A nickel-catalyzed route to pyridines

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; NICKEL; NITRILE; PYRIDINE DERIVATIVE;

EID: 17144426927     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0508931     Document Type: Article
Times cited : (210)

References (34)
  • 15
    • 0034609693 scopus 로고    scopus 로고
    • Milder reaction conditions can be employed with modified Co catalysts; however, these catalysts are not readily available. For example, the preparation involves purification by column chromatography under an inert atmosphere: Fatland, A. W.; Eaton, B. E. Org. Lett. 2000, 2, 3131.
    • (2000) Org. Lett. , vol.2 , pp. 3131
    • Fatland, A.W.1    Eaton, B.E.2
  • 25
    • 4043179055 scopus 로고    scopus 로고
    • Ni complexes readily undergo oxidative addition of both alkyl- and aryl- CN bonds. For example, Ni complexes catalyze the carbocyanation of alkynes: (a) García, J. J.; Arévalo, A.; Brunkan, N. M.; Jones, W. D. Organometallics 2004, 23, 3997.
    • (2004) Organometallics , vol.23 , pp. 3997
    • García, J.J.1    Arévalo, A.2    Brunkan, N.M.3    Jones, W.D.4
  • 28
    • 17144398186 scopus 로고    scopus 로고
    • note
    • Ni complexes are known to cause homodimerization of nitriles (see ref 9).
  • 29
    • 17144430616 scopus 로고    scopus 로고
    • note
    • Both SIPr and IPr ligands readily dissociate from Ni(0). even upon the addition of COD (see ref 10a).
  • 30
    • 17144403953 scopus 로고    scopus 로고
    • note
    • Unsaturated analogue IPr gave slightly lower conversion under identical reaction conditions (99% versus 66% for SIPr and IPr, respectively) (IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene; SIPr = 1,3-bis-(2,6- diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene).
  • 31
    • 17144375422 scopus 로고    scopus 로고
    • note
    • This is in contrast to the Ni/NHC-catalyzed route to pyridones where electron-deficient isocyanates required elevated temperatures for complete cycloaddition (see ref 11).
  • 34
    • 17144401250 scopus 로고    scopus 로고
    • note
    • Cycloaddition with acetonitrile (2e) afforded 2,3,4,5-tetraethyl-6- methylpyridine (25) in 25% yield. See Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.