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Volumn 64, Issue 4, 1999, Pages 649-672

Coupling reactions of ortho-substituted halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes

Author keywords

Alkynes; Arenes; Cross coupling reactions; Diphenylacetylenes; Halobenzenes; Palladium catalysis; Phenylacetylenes

Indexed keywords


EID: 0033247621     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc19990649     Document Type: Article
Times cited : (6)

References (31)
  • 1
    • 0000509322 scopus 로고
    • B. M. Trost, I. Fleming and L. A. Paquette, Eds, Chap. 2.4. Pergamon Press, Oxford
    • For reviews see, e.g.: a) Sonogashira K. in: Comprehensive Organic Synthesis (B. M. Trost, I. Fleming and L. A. Paquette, Eds), Vol. 3, Chap. 2.4, p. 521. Pergamon Press, Oxford 1991;
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 521
    • Sonogashira, K.1
  • 10
    • 0000249493 scopus 로고    scopus 로고
    • M. Beller and C. Bolm, Eds, Chap. 2.10. Wiley-VCH, Weinheim
    • e) Geisler H. in: Transition Metals for Organic Synthesis (M. Beller and C. Bolm, Eds), Vol. 1, Chap. 2.10, p. 158. Wiley-VCH, Weinheim 1998;
    • (1998) Transition Metals for Organic Synthesis , vol.1 , pp. 158
    • Geisler, H.1
  • 11
    • 0002769275 scopus 로고    scopus 로고
    • F. Diederich and P. J. Stang, Eds, Chap. 5. Wiley-VCH, Weinheim
    • f) Sonogashira K. in: Metal-Catalyzed Cross-Coupling Reactions (F. Diederich and P. J. Stang, Eds), Chap. 5, p. 203. Wiley-VCH, Weinheim 1998.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203
    • Sonogashira, K.1
  • 16
    • 0000725544 scopus 로고    scopus 로고
    • F. Diederich and P. J. Stang, Eds, Chap. 4. Wiley-VCH, Weinheim
    • Mitchell T. N. in: Metal-Catalyzed Cross-Coupling Reactions (F. Diederich and P. J. Stang, Eds), Chap. 4, p. 167. Wiley-VCH, Weinheim 1998.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 167
    • Mitchell, T.N.1
  • 18
    • 85033952934 scopus 로고    scopus 로고
    • note
    • The use of diisopropylamine instead of piperidine to avoid aminolysis of ester groups does not lead to a better yield of 35. This compound is not affordable by homo-coupling of 15 with gaseous acetylene under Pd or Pd/Cu catalysis.
  • 29
    • 85033949773 scopus 로고    scopus 로고
    • note
    • Bubbling of gaseous acetylene (purified by passing through a dry-ice trap, concentrated sulfuric acid, and potassium hydroxide pellets) into the reaction mixture led to reduced yields of coupled products.
  • 30
    • 85033966017 scopus 로고    scopus 로고
    • note
    • 2/CuI-catalyzed coupling of methyl 2-bromobenzoate 1a with (trimethylsilyl)acetylene in the presence of carefully purified triethylamine (1.5 equivalent) in THF at room temperature provided 23a in 88% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.