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Volumn 21, Issue 20, 2002, Pages 4169-4181

Ferrocene-based heteronuclear bidentate Lewis acids via highly selective ortho-borylation of 1,1′-bis(trimethylstannyl)ferrocene

Author keywords

[No Author keywords available]

Indexed keywords

BORYLATION; LEWIS ACIDS;

EID: 0001074367     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0204890     Document Type: Article
Times cited : (49)

References (92)
  • 11
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    • For reviews on the use of bifunctional Lewis acids in Ziegler-Natta polymerization see: (j) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
    • (2000) Chem. Rev. , vol.100 , pp. 1391
    • Chen, E.Y.-X.1    Marks, T.J.2
  • 35
    • 0003937934 scopus 로고
    • John Wiley & Sons: Chichester
    • Notable exceptions include reactions involving the replacement of a sterically demanding group by a proton (release of steric strain leads to steric acceleration) and the formation of an intermediate complex between the solvent and the substituent, thereby leading to a strong +I effect of this group. The latter effect is for example believed to be responsible for the observed ortho-selectivity in the nitration of phenylboronic acid. See: Taylor, R. Electrophilic Aromatic Substitution; John Wiley & Sons: Chichester, 1990.
    • (1990) Electrophilic Aromatic Substitution
    • Taylor, R.1
  • 36
    • 0034617037 scopus 로고    scopus 로고
    • For recent studies of regioselective electrophilic aromatic substitution reactions, see for example: (a) Yonehara, F.; Kido, Y.; Yamaguchi, M. Chem. Commun. 2000, 1189.
    • (2000) Chem. Commun. , pp. 1189
    • Yonehara, F.1    Kido, Y.2    Yamaguchi, M.3
  • 45
    • 20244389130 scopus 로고    scopus 로고
    • note
    • The 1-stannyl-2-borylferrocenes and 1-stannyl-3-borylferrocenes form as racemic mixtures as a result of their planar chirality. Only one of the two enantiomers will be shown in the schemes and figures.
  • 51
    • 20244371633 scopus 로고    scopus 로고
    • note
    • The pseudotriplet at δ = 4.46 (J = 1.2 Hz) for isomer 2b-Cl is overlapping with the double doublet at δ = 4.46 for isomer 2a-Cl. The signal is clearly visible in enriched samples of 2b-Cl, and the assignment has been further confirmed by 2D NMR spectroscopy (dqfCOSY). The CpSn-H2, 5 protons for 2c-Cl resonate outside the spectral range shown in Figure 1 at δ = 3.88.
  • 57
    • 20244375213 scopus 로고    scopus 로고
    • note
    • More detailed mechanistic studies are currently under way and will be reported in a future contribution.
  • 60
    • 0000439481 scopus 로고
    • For related heteronuclear bifunctional Lewis acids with an organic backbone, see for example ref 10 and the following: (a) Katz, H. E. J. Am. Chem. Soc. 1986, 108, 7640.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7640
    • Katz, H.E.1
  • 63
    • 0034675610 scopus 로고    scopus 로고
    • A similar phenomenon has been observed for the reaction of stannylated zirconocenes with boron halides and for the borylation of 1,2-bis(trimethylstannyl)benzene: (a) Cheng, X.; Slebodnick, C.; Deck, P. A.; Billodeaux, D. R.; Fronczek, F. R. Inorg. Chem. 2000, 39, 4921.
    • (2000) Inorg. Chem. , vol.39 , pp. 4921
    • Cheng, X.1    Slebodnick, C.2    Deck, P.A.3    Billodeaux, D.R.4    Fronczek, F.R.5
  • 65
    • 20244387534 scopus 로고    scopus 로고
    • See ref 35b
    • See ref 35b.
  • 75
    • 84989447115 scopus 로고
    • For examples of intramolecular π-coordination of an alkynyl group to an organotin cation see: (a) Wrackmeyer, B.; Kundler, S.; Milius, W.; Boese, R. Chem. Ber. 1994, 127, 333.
    • (1994) Chem. Ber. , vol.127 , pp. 333
    • Wrackmeyer, B.1    Kundler, S.2    Milius, W.3    Boese, R.4
  • 82
    • 20244362317 scopus 로고    scopus 로고
    • note
    • The assignments of the Cp protons have been further confirmed through the presence of a cross-peak between the Cp-H2 protons and the ortho-protons on the phenyl group in the NOESY spectrum of 3a-Ph.
  • 85
    • 0000984665 scopus 로고    scopus 로고
    • For a rare example of a complex between an enantiomerically pure planar-chiral Lewie acid and a chiral Lewis base see: Tweddell, J.; Hoic, D. A.; Fu, G. C. J. Org. Chem. 1997, 62, 8286.
    • (1997) J. Org. Chem. , vol.62 , pp. 8286
    • Tweddell, J.1    Hoic, D.A.2    Fu, G.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.