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Volumn 70, Issue 11, 2012, Pages 1123-1133

Experimental and theoretical studies on regiocontrol of benzyne reactions using silyl and boryl directing groups

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTION; DIRECTING GROUPS; ELECTROSTATIC EFFECT; NATURAL BOND ORBITAL; NUCLEOPHILIC ADDITIONS; REACTION PATHWAYS; THEORETICAL STUDY; TRANSITION STATE;

EID: 84875961665     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.70.1123     Document Type: Article
Times cited : (19)

References (85)
  • 21
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    • Selected silyl-directed reactions
    • Selected silyl-directed reactions: Boebel, T. A.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 7534.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 7534
    • Boebel, T.A.1    Hartwig, J.F.2
  • 26
    • 27144453787 scopus 로고    scopus 로고
    • The DA Reaction Between 3-.uoro-6-(trimethylsilyl)benzyne And 2-(trimethylsilyl)furan Was Reported To Exclusively Generate 15-Bis(trimethylsilyl)-14-Epoxy-8-Fluoro-14-Dihydronaphthalene. However The DA Reaction Of The Simple 3-(trimethylsilyl)benzyne Was Not Examined See
    • The DA reaction between 3-.uoro-6-(trimethylsilyl)benzyne and 2-(trimethylsilyl)furan was reported to exclusively generate 1,5-bis(trimethylsilyl)-1,4-epoxy-8-fluoro-1,4-dihydronaphthalene. However, the DA reaction of the simple 3-(trimethylsilyl)benzyne was not examined, see: Masson, E.; Schlosser, M. Eur. J. Org. Chem. 2005, 4401.
    • (2005) Eur. J. Org. Chem. , pp. 4401
    • Masson, E.1    Schlosser, M.2
  • 38
    • 0011475330 scopus 로고
    • Some other examples of the DA reactions of benzynes having a bulky group
    • Some other examples of the DA reactions of benzynes having a bulky group: Franck, R. W.; Leser, E. G. J. Org. Chem. 1970, 35, 3932.
    • (1970) J. Org. Chem. , vol.35 , pp. 3932
    • Franck, R.W.1    Leser, E.G.2
  • 48
    • 0000407471 scopus 로고
    • For some examples of acid-catalyzed opening of 1,4-epoxy-1,4- dihydronaphthalenes
    • For some examples of acid-catalyzed opening of 1,4-epoxy-1,4- dihydronaphthalenes, see: Batt, D. G.; Jones, D. G.; La Greca, S. J. Org. Chem. 1991, 56, 6704.
    • (1991) J. Org. Chem. , vol.56 , pp. 6704
    • Batt, D.G.1    Jones, D.G.2    La Greca, S.3
  • 52
    • 33750494972 scopus 로고    scopus 로고
    • For examples of intermolecular. uoride-free Hiyama reactions, see
    • For examples of intermolecular. uoride-free Hiyama reactions, see: Alacid, E.; Nájera, C. Adv. Synth. Catal. 2006, 348, 2085.
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 2085
    • Alacid, E.1    Nájera, C.2
  • 53
    • 77956914995 scopus 로고    scopus 로고
    • After the publication of our work, the following paper was published
    • After the publication of our work, the following paper was published: Tsubouchi, A.; Matsuda, H.; Kira, T.; Takeda, T. Chem. Lett. 2009, 38, 1180.
    • (2009) Chem. Lett. , vol.38 , pp. 1180
    • Tsubouchi, A.1    Matsuda, H.2    Kira, T.3    Takeda, T.4
  • 65
    • 0000293830 scopus 로고
    • For the only example of a DA reaction of an unsymmetrically substituted benzyne with pyrrole, see
    • For the only example of a DA reaction of an unsymmetrically substituted benzyne with pyrrole, see: Gribble, G. W.; Kelly, W. J. Tetrahe-dron Lett. 1985, 26, 3779.
    • (1985) Tetrahe-dron Lett , vol.26 , pp. 3779
    • Gribble, G.W.1    Kelly, W.J.2
  • 69
    • 34250821724 scopus 로고    scopus 로고
    • For selected examples for [3+2] cycloaddition of benzynes
    • For selected examples for [3+2] cycloaddition of benzynes: Jin, T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2007, 46, 3323.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3323
    • Jin, T.1    Yamamoto, Y.2
  • 76
    • 53149116233 scopus 로고    scopus 로고
    • The reaction of 3-silylbenzynes 7A with nitrones 36, which had been reported by Suzuki 11 and Danishefsky under harsh reaction conditions, also gave benzisoxazoles 39A with high selectivity, see
    • The reaction of 3-silylbenzynes 7A with nitrones 36, which had been reported by Suzuki 11 and Danishefsky under harsh reaction conditions, also gave benzisoxazoles 39A with high selectivity, see: Dai, M.; Wang, Z.; Danishefsky, S. J. Tetrahedron Lett. 2008, 49, 6613.
    • (2008) Tetrahedron Lett , vol.49 , pp. 6613
    • Dai, M.1    Wang, Z.2    Danishefsky, S.J.3
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    • Optimized structures of reactants, TSs, and products were characterized by analytical frequency calculations, and all total electronic energies of these species were included in the zero-point energy corrections at the same level. The calculated number of imaginary frequencies (NImag) determine whether the optimized structures are energy minima (NImag=0) or TSs (NImag=1) along the reaction pathway
    • Optimized structures of reactants, TSs, and products were characterized by analytical frequency calculations, and all total electronic energies of these species were included in the zero-point energy corrections at the same level. The calculated number of imaginary frequencies (NImag) determine whether the optimized structures are energy minima (NImag=0) or TSs (NImag=1) along the reaction pathway.


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