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Volumn 30, Issue 7, 2011, Pages 1896-1901

Comparison of imine to olefin insertion reactions: Generation of five- and six-membered lactams via a nickel-mediated co, olefin, co, imine insertion cascade

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COMPLEXES; ALKENE INSERTION; ELECTRONIC INFLUENCE; IMINE COORDINATION; IN-SITU; INSERTION REACTIONS; MIGRATORY INSERTION; NICKEL COMPLEX; NITROGEN DONORS;

EID: 79953711475     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1011566     Document Type: Article
Times cited : (8)

References (52)
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    • 1542317840 scopus 로고    scopus 로고
    • For related stoichiometric imine insertions into late-metal-carbon bonds, see
    • For related stoichiometric imine insertions into late-metal-carbon bonds, see: Krug, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 2694
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2694
    • Krug, C.1    Hartwig, J.F.2
  • 36
    • 34548079784 scopus 로고    scopus 로고
    • For the alternating copolymerization of imines and CO, see
    • For the alternating copolymerization of imines and CO, see: Sun, H.; Zhang, J.; Liu, Q.; Yu, L.; Zhao, J. Angew. Chem., Int. Ed. 2007, 46, 6068
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 6068
    • Sun, H.1    Zhang, J.2    Liu, Q.3    Yu, L.4    Zhao, J.5
  • 37
    • 84909530809 scopus 로고
    • On the basis of 72.8 and 147 kcal/mol for an average C-N bond and C=N bond, respectively: Bond; Pati, S., Ed.; Wiley: New York
    • On the basis of 72.8 and 147 kcal/mol for an average C-N bond and C=N bond, respectively: Sandorfy, C. The Chemistry of the Carbon-Nitrogen Double Bond; Pati, S., Ed.; Wiley: New York, 1970; p 1.
    • (1970) The Chemistry of the Carbon-Nitrogen Double Bond , pp. 1
    • Sandorfy, C.1
  • 39
    • 79953724279 scopus 로고    scopus 로고
    • note
    • 2-coordinated imine, or a combination of these. Nevertheless, the generation of the formal imine insertion product is a reaction with a higher barrier than that with simple alkenes. We thank a reviewer for noting this.
  • 40
    • 0030567643 scopus 로고    scopus 로고
    • Styrene typically undergoes nickel-catalyzed oligomerization at room temperature in 0.1-2 h
    • Styrene typically undergoes nickel-catalyzed oligomerization at room temperature in 0.1-2 h: Ascenso, J. A.; Dias, A. R.; Gomes, P. T. Macromolecules 1996, 29, 4172
    • (1996) Macromolecules , vol.29 , pp. 4172
    • Ascenso, J.A.1    Dias, A.R.2    Gomes, P.T.3
  • 42
    • 79953690438 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis shows it to be analogous to previously generated nickel-acyl complexes: (8): see the Experimental Section for details.
  • 43
    • 79953721602 scopus 로고    scopus 로고
    • note
    • 3CO- reasonances. While products 8 and 10 could not be separated for full characterization, these data are similar to those for previously isolated metal-chelated amides, (8, 9) and cleavage of the amide ligands with KCN/MeOH was used to confirm the amide ligand structure.
  • 44
    • 79953694986 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 52
    • 79953711661 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.