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Volumn 78, Issue 7, 2013, Pages 2965-2983

Regiocomplementary cycloaddition reactions of boryl- and silylbenzynes with 1,3-dipoles: Selective synthesis of benzo-fused azole derivatives

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; DENSITY FUNCTIONAL THEORY;

EID: 84875931965     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302802b     Document Type: Article
Times cited : (75)

References (61)
  • 28
    • 84865619212 scopus 로고    scopus 로고
    • Garg and Houk et al. and our group have independently studied the (3 + 2) cycloaddition reactions of 3-silylbenzynes with 1,3-dipoles along with computational analyses, and both of our groups have come to essentially the same conclusions. See: Bronner, S. M.; Mackey, J. L.; Houk, K. N.; Garg, N. K. J. Am. Chem. Soc. 2012, 134, 13966-13969
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 13966-13969
    • Bronner, S.M.1    MacKey, J.L.2    Houk, K.N.3    Garg, N.K.4
  • 29
    • 84871587367 scopus 로고    scopus 로고
    • Very recently, Garg et al. achieved regioselective (3 + 2) cycloadditions of pyridynes possessing either a sulfamoyloxy group or a bromo group as a directing group; see: Goetz, A. E.; Garg, N. K. Nat. Chem. 2013, 5, 54-60
    • (2013) Nat. Chem. , vol.5 , pp. 54-60
    • Goetz, A.E.1    Garg, N.K.2
  • 40
  • 42
    • 84875948521 scopus 로고    scopus 로고
    • Frisch, M. J.; see the Supporting Information for full citation
    • All DFT calculations were performed at the B3LYP/6-31G(d) level except for iodine atom (B3LYP/LanL2DZ) of 6k, TS17, and TS18. Optimized structures of the reactants, transition sates, and products were characterised by analytical frequency calculations, and all the total electronic energies were included in the zero-point energy corrections at the same level. The calculated number of imaginary frequencies (NImag) will determine whether the optimized structures are the energy minima (NImag = 0) or transition states (NImag = 1) along the reaction pathway. All calculations were carried out by using the Gaussian 09 revision A.02 (Frisch, M. J.; see the Supporting Information for full citation).
  • 46
    • 84859911641 scopus 로고    scopus 로고
    • ⧧ values of the (3 + 2) cycloaddition reactions of silylbenzynes 5 were applied for the calculation - 1409
    • ⧧ values of the (3 + 2) cycloaddition reactions of silylbenzynes 5 were applied for the calculation
    • (2012) ChemPhysChem , vol.13 , pp. 1407
    • Grimme, S.1
  • 47
    • 70349347859 scopus 로고    scopus 로고
    • All graphics were prepared with CYLview: Université de Sherbrooke.
    • All graphics were prepared with CYLview: CYLview, 1.0b; Legault, C. Y. Université de Sherbrooke, 2009, (http://www.cylview.org).
    • (2009) CYLview, 1.0b
    • Legault, C.Y.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.