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Volumn 71, Issue 5, 2006, Pages 2188-2191

An improved method for the bromination of metalated haloarenes via lithium, zinc transmetalation: A convenient synthesis of 1,2-dibromoarenes

Author keywords

[No Author keywords available]

Indexed keywords

1,2-DIBROMOARENES; ARYLZINC SPECIES; BROMINATION;

EID: 33644638474     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052515k     Document Type: Article
Times cited : (42)

References (52)
  • 13
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    • (a) March, J. Aromatic Electrophilic Substitution. In Advanced Organic Chemistry, 4th ed.; Wiley & Sons: New York, 1992; pp 507-511.
    • (1992) Advanced Organic Chemistry, 4th Ed. , pp. 507-511
    • March, J.1
  • 15
    • 84956646927 scopus 로고
    • Formation of carbon-halogen bond
    • Patai, S., Rappoport, Z., Eds.; The Chemistry of Functional Groups; Wiley & Sons: Chichester, U.K., Chapter 22
    • (a) Hudlicky, M.; Hudlicky, T. Formation of Carbon-Halogen Bond. In Supplement D: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.; The Chemistry of Functional Groups; Wiley & Sons: Chichester, U.K., 1983: Chapter 22, pp 1021-1172.
    • (1983) Supplement D: The Chemistry of Halides, Pseudohalides and Azides , pp. 1021-1172
    • Hudlicky, M.1    Hudlicky, T.2
  • 16
    • 0000883697 scopus 로고
    • Formation of carbon-halogen bonds (Cl, Br, I)
    • Patai, S., Rappoport, Z., Eds.; The Chemistry of Functional Groups; Wiley & Sons: Chichester, U.K., Chapter 11
    • (b) Sasson, Y. Formation of Carbon-Halogen Bonds (Cl, Br, I). In Supplements D2: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.; The Chemistry of Functional Groups; Wiley & Sons: Chichester, U.K., 1995; Chapter 11, pp 535-628.
    • (1995) Supplements D2: The Chemistry of Halides, Pseudohalides and Azides , pp. 535-628
    • Sasson, Y.1
  • 32
    • 12344258124 scopus 로고    scopus 로고
    • and references therein
    • (a) Polybrominated arene formation under strong basic conditions: Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376 and references therein.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 376
    • Schlosser, M.1
  • 34
    • 33644643454 scopus 로고    scopus 로고
    • note
    • All products have been identified by GC/MS.
  • 35
    • 33644660333 scopus 로고    scopus 로고
    • note
    • 2 solution that afforded 3-chloro-1,2-dibromo-3- chlorobenzene (4a) in 94% assay yield.
  • 36
    • 33644650150 scopus 로고    scopus 로고
    • note
    • At the same time only small amounts of side products (1a and 6) according to Scheme 1 were observed.
  • 37
    • 33644653522 scopus 로고    scopus 로고
    • note
    • 13C NMR data confirmed that within 20 min the deprotonation reaction primarily formed the lithiated product 2b.
  • 38
    • 0000844123 scopus 로고    scopus 로고
    • and references therein
    • For examples of lithium-zinc transmetalation and Negishi-type cross-coupling reactions, see: (a) Karig, G.; Spencer, J. A.; Gallagher, T. Org. Lett. 2001, 3, 835 and references therein.
    • (2001) Org. Lett. , vol.3 , pp. 835
    • Karig, G.1    Spencer, J.A.2    Gallagher, T.3
  • 39
    • 33644653832 scopus 로고    scopus 로고
    • note
    • (b) Examples for the cross-coupling reaction of (2-bromophenyl)(iodo)zinc were described in ref 24.
  • 40
    • 33644651079 scopus 로고    scopus 로고
    • note
    • 1,3-Bromofluorobenzene (1b) was chosen for the NMR experiment, because the formation of 2-bromo-6-fluorophenyllithium (2b) appeared as a homogeneous reaction mixture under the standard reaction conditions.
  • 45
    • 0003975691 scopus 로고
    • Academic Press: New York
    • Typically, ortho-lithiated bromoarenes are plagued by low thermodynamic stability, which can lead to debromination via a benzyne pathway: (a) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
    • (1967) Dehydrobenzene and Cycloalkynes
    • Hoffmann, R.W.1
  • 51
    • 33644642160 scopus 로고    scopus 로고
    • note
    • The same regioselectivity in the deprotonation step with LiTMP has been observed: ref 12(b).
  • 52
    • 33644650807 scopus 로고    scopus 로고
    • note
    • The lithiated methyl-3-bromobenzoate (2g) underwent self-conden sation as the major side product after bromination was initiated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.