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Volumn 68, Issue 24, 2003, Pages 9513-9516

Synthesis of 2,3-Substituted Thienylboronic Acids and Esters

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; ESTERS; HALOGEN COMPOUNDS; MAGNESIUM PRINTING PLATES; PALLADIUM; QUENCHING;

EID: 0345686421     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034919n     Document Type: Article
Times cited : (47)

References (56)
  • 4
    • 85069075615 scopus 로고    scopus 로고
    • (b) Negwer Database on http://cwgen.chemweb.com/negwersearch.html.
    • Negwer Database
  • 5
    • 0003443858 scopus 로고    scopus 로고
    • Swiss Pharmaceutical Society, Ed.; Medpharm Scientific Publishers: Stuttgart
    • (c) Index Nominum 2000, International Drug Directory; Swiss Pharmaceutical Society, Ed.; Medpharm Scientific Publishers: Stuttgart, 2000.
    • (2000) Index Nominum 2000, International Drug Directory
  • 25
    • 0040261385 scopus 로고
    • The three isomeric dibromothiophenes are commercially available. 2-Bromo-3-iodothiophene can be prepared according to ref 8c. 2-Bromo-4-iodothiophene can be prepared according to: Gronowitz, S.; Holm, B. Acta Chem. Scand. 1976, B30, 505-511.
    • (1976) Acta Chem. Scand. , vol.B30 , pp. 505-511
    • Gronowitz, S.1    Holm, B.2
  • 26
    • 0345189406 scopus 로고
    • 3-Bromo-2-chlorothiophene can be prepared according to: Gronowitz, S.; Holm, B. Acta Chem. Scand. 1976, B30, 423-429.
    • (1976) Acta Chem. Scand. , vol.B30 , pp. 423-429
    • Gronowitz, S.1    Holm, B.2
  • 30
    • 0001786881 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim
    • (c) Suzuki, A. In Metal-catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 49-97.
    • (1998) Metal-catalyzed Cross-Coupling Reactions , pp. 49-97
    • Suzuki, A.1
  • 43
    • 85069081349 scopus 로고    scopus 로고
    • note
    • The protonation of the active Grignard species resulting in 2-bromothiophene and 3-bromothiophene may be a result of elimination of hydrogen bromide and hydrogen iodide from ethyl bromide and ethyl iodide by reaction with 2-bromo-3-thienylmagnesium chloride and 3-bromo-2-thienylmagnesium chloride, respectively.
  • 45
    • 85069072438 scopus 로고    scopus 로고
    • note
    • 1) δ 7.11 (d, J = 4.9 Hz, 1 H), 7.54 (d, J = 4.9 Hz, 1 H). These data are in accordance with the data observed for the byproduct in 8b.
  • 47
    • 0003598094 scopus 로고
    • Scheffold, R., Ed.; John Wiley & Sons: New York
    • 4: Normant, J. F.; Cahiez, G. In Organomanganese Reagents in Modern Synthetic Methods; Scheffold, R., Ed.; John Wiley & Sons: New York, 1983; Vol. 3, pp 173-216. However, 2-bromo-3-thienylmanganese chloride did not react with acetic anhydride, indicating a very low reactivity of this organometallic species.
    • (1983) Organomanganese Reagents in Modern Synthetic Methods , vol.3 , pp. 173-216
    • Normant, J.F.1    Cahiez, G.2
  • 53
    • 85069079532 scopus 로고    scopus 로고
    • note
    • 3 = tri(tertbutyl)phosphine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.