메뉴 건너뛰기




Volumn 132, Issue 17, 2010, Pages 6001-6005

Nature of intermediates in organo-somo catalysis of α-arylation of aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SYSTEM; ARYLATIONS; ENAMINES; EXPERIMENTAL OBSERVATION; FUNCTIONALS; ORTHO SELECTIVITY; RADICAL CATIONS; SPIN DENSITIES; TRANSITION STRUCTURES;

EID: 77951688144     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9063074     Document Type: Article
Times cited : (107)

References (27)
  • 7
    • 70149099966 scopus 로고    scopus 로고
    • Correction
    • Correction: J. Am. Chem. Soc. 2009, 131, 6640.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 6640
  • 9
    • 77951691798 scopus 로고    scopus 로고
    • The authors of ref 1f used (2 R,5 R)- 2 as the catalyst. Because our calculations and experiments were performed with the opposite enantiomer, this paper reports the study of catalyst (2 S,5 S)- 2
    • The authors of ref 1f used (2 R,5 R)- 2 as the catalyst. Because our calculations and experiments were performed with the opposite enantiomer, this paper reports the study of catalyst (2 S,5 S)- 2.
  • 10
    • 1842661169 scopus 로고
    • For ortho -selective radical additions to aromatics, see: Abramovitch, R. A., Ed.; Plenum Press: New York
    • For ortho -selective radical additions to aromatics, see: Tiecco, M. and Testaferri, L. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, p 61.
    • (1983) Reactive Intermediates , vol.3 , pp. 61
    • Tiecco, M.1    Testaferri, L.2
  • 13
    • 0003374018 scopus 로고
    • For a study of the stability of cyclohexadienyl radicals, see
    • For a study of the stability of cyclohexadienyl radicals, see: Birch, A. J., Hinde, A. L., and Radom, L. J. Am. Chem. Soc. 1980, 102, 4074
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4074
    • Birch, A.J.1    Hinde, A.L.2    Radom, L.3
  • 14
    • 0038626673 scopus 로고    scopus 로고
    • With the exceptions of 14, 15- E, 15- Z, and 19* - 24, which were optimized in the gas phase, all of the geometries were optimized in water (CPCM model) using DFT at the UB3LYP/6-31G(d) level, as implemented in the Gaussian03 suite of programs (; et al., revision C.02; Gaussian, Inc.: Wallingford, CT). Model cations and radicals 19* - 24* were optimized using both CBS-QB3 (Gaussian 03) and UB3LYP/6-31G(d). All of the stationary points were verified by vibrational frequency analysis. Single-point calculations were also performed using M06-2X/6-31+G(d), as implemented in Gaussian09 (; et al. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009). Each of the computed structures is designated with an asterisk (). The resulting energies are reported in kcal/mol in all figures and schemes
    • With the exceptions of 14, 15- E, 15- Z, and 19* - 24 which were optimized in the gas phase, all of the geometries were optimized in water (CPCM model) using DFT at the UB3LYP/6-31G(d) level, as implemented in the Gaussian03 suite of programs (Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004). Model cations and radicals 19* - 24* were optimized using both CBS-QB3 (Gaussian 03) and UB3LYP/6-31G(d). All of the stationary points were verified by vibrational frequency analysis. Single-point calculations were also performed using M06-2X/6-31+G(d), as implemented in Gaussian09 (Frisch, M. J.; et al. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009). Each of the computed structures is designated with an asterisk (). The resulting energies are reported in kcal/mol in all figures and schemes.
    • (2004) Gaussian 03
    • Frisch, M.J.1    Frisch, M.J.2
  • 18
    • 77951672247 scopus 로고    scopus 로고
    • Unpublished results
    • Unpublished results.
  • 19
    • 77951689575 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 20
    • 0033606254 scopus 로고    scopus 로고
    • For an example of water-assisted reactivity of radical cations, see
    • For an example of water-assisted reactivity of radical cations, see: Heinemann, C. and Demuth, M. J. Am. Chem. Soc. 1999, 121, 4894
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4894
    • Heinemann, C.1    Demuth, M.2
  • 21
    • 77951687344 scopus 로고    scopus 로고
    • This study is underway and will be reported in due course
    • This study is underway and will be reported in due course.
  • 25
    • 0001486103 scopus 로고    scopus 로고
    • The preferred planar methoxy conformation holds true for anisole. For example, see
    • The preferred planar methoxy conformation holds true for anisole. For example, see: Emsley, J. W., Foord, E. K., and Lindon, J. C. J. Chem. Soc., Perkin Trans. 2 1998, 1211
    • (1998) J. Chem. Soc., Perkin Trans. 2 , pp. 1211
    • Emsley, J.W.1    Foord, E.K.2    Lindon, J.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.