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Volumn 369, Issue 1, 2011, Pages 2-14

Theoretical studies of regioselectivity of Ni- and Rh-catalyzed C-C bond forming reactions with unsymmetrical alkynes

Author keywords

Cycloadditions; Density functional theory; Reductive couplings; Regioselectivity; Transition metal catalysis

Indexed keywords

CATALYSIS; COORDINATION REACTIONS; COUPLINGS; HYDROCARBONS; NICKEL COMPOUNDS; REGIOSELECTIVITY; RHODIUM COMPOUNDS; SUBSTRATES; TRANSITION METALS;

EID: 79953874235     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2010.12.042     Document Type: Review
Times cited : (24)

References (105)
  • 5
  • 25
    • 0041464227 scopus 로고    scopus 로고
    • For a review on transition metal-alkyne bonding interactions, see: G. Frenking, and N. Frohlich Chem. Rev. 100 2000 717
    • (2000) Chem. Rev. , vol.100 , pp. 717
    • Frenking, G.1    Frohlich, N.2
  • 35
  • 37
    • 79953860307 scopus 로고    scopus 로고
    • See Refs. [8h,8i].
    • See Refs. [8h,8i].
  • 43
    • 79953902636 scopus 로고    scopus 로고
    • See Refs. [4] and [5].
    • See Refs. [4] and [5].
  • 50
    • 79953861292 scopus 로고    scopus 로고
    • See Ref. [4].
    • See Ref. [4].
  • 56
    • 79953904668 scopus 로고    scopus 로고
    • See Ref. [6].
    • See Ref. [6].
  • 57
    • 0037538818 scopus 로고    scopus 로고
    • For other Ni-catalyzed intermolecular reductive alkyne-aldehyde couplings, see: K. Takai, S. Sakamoto, and T. Isshiki Org. Lett. 5 2003 653
    • (2003) Org. Lett. , vol.5 , pp. 653
    • Takai, K.1    Sakamoto, S.2    Isshiki, T.3
  • 75
    • 79953898841 scopus 로고    scopus 로고
    • See Ref. [7].
    • See Ref. [7].
  • 76
    • 79953906882 scopus 로고    scopus 로고
    • note
    • For example, in Rh(I)-catalyzed hydrogenative couplings of 1,3-diynes and carbonyl partners, the regioselectivity is determined by the oxidative cyclization step (Fig. 1b), while the rate-determining step is subsequent σ-bond metathesis of the metallacycle intermediate. See Ref. [21].
  • 79
    • 79953900495 scopus 로고    scopus 로고
    • note
    • 2 in terms of Gibbs free energy, 7.6 kcal/mol less stable in terms of enthalpy.
  • 92
    • 79953853981 scopus 로고    scopus 로고
    • Ni: See Refs. [12b], [12d], [13a], and [14a]
    • Ni: See Refs. [12b], [12d], [13a], and [14a].
  • 95
    • 79953849327 scopus 로고    scopus 로고
    • note
    • While 1,6-enynes show strong directing effects in Ni-catalyzed ligand-free reductive couplings, those enynes with shorter one- or two-atom tethers are not reactive under the same conditions. See Ref. [4b].
  • 100
    • 79953888821 scopus 로고    scopus 로고
    • See Refs. [15b], [15c], [15f], and [15h].
    • See Refs. [15b], [15c], [15f], and [15h].
  • 101
    • 0038626673 scopus 로고    scopus 로고
    • Revision D.01: Frisch, M. J. et al. Gaussian, Inc., Wallingford CT
    • Gaussian 03, Revision D.01: Frisch, M. J. et al. Gaussian, Inc., Wallingford CT, 2004.
    • (2004) Gaussian 03


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.