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Volumn 127, Issue 30, 2005, Pages 10476-10477

The Ni-mediated cyclocarbonylation of allyl halides and alkynes made catalytic. Evidence supporting the involvement of pseudoradical NiI species in the mechanism

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ALLYL COMPOUND; HALIDE; NICKEL; RADICAL;

EID: 23044487249     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0525713     Document Type: Article
Times cited : (28)

References (26)
  • 3
    • 0001717548 scopus 로고    scopus 로고
    • (c) For Ni-catalyzed Pauson-Khand-type reactions, see: Zhang, M.; Buchwald, S. L. J. Org. Chem. 1996, 61, 4498-4499.
    • (1996) J. Org. Chem. , vol.61 , pp. 4498-4499
    • Zhang, M.1    Buchwald, S.L.2
  • 13
    • 33444459098 scopus 로고
    • Protonolysis or "substitutive reduction" is one of the concurrent processes responsible for Ni oxidation: Chiusoli, G. P.; Bottaccio, G.; Cameroni, A. Chim. Ind. (Milan) 1962, 44, 131-135.
    • (1962) Chim. Ind. (Milan) , vol.44 , pp. 131-135
    • Chiusoli, G.P.1    Bottaccio, G.2    Cameroni, A.3
  • 23
    • 0039710774 scopus 로고
    • In some Ni complexes with a formally odd oxidation state for the metal, the unpaired electron is fully localized on the ligand, and the complex is Ni-silent. See, for instance: Kreisman, P.; Marsh, R.; Preer, J. R.; Gray, H. B. J. Am. Chem. Soc. 1968, 90, 1067-1068.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1067-1068
    • Kreisman, P.1    Marsh, R.2    Preer, J.R.3    Gray, H.B.4
  • 24
    • 33444478656 scopus 로고    scopus 로고
    • note
    • Although, initially, an excess of iodide was added only to solubilize the Ni salt as tetraiodonickelate, the presence of iodide has proven to activate the reaction and is liable to operate as well as an efficient allyl activator and/or a stabilizing ligand. Without it, the reaction proceeds sluggishly.
  • 26
    • 33444456622 scopus 로고    scopus 로고
    • note
    • -1 in the IR spectrum not present in the final adduct. The Mössbauer spectrum accounts for at least 85% of the dissolved iron as Fe(II). The reflux of the crude product in THF with an excess of paraformaldehyde gave 40% of 3-hydroxy-2-[5-(2-phenylcyclopent-2-enonyl)]propionic acid (one single isomer).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.