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Volumn 75, Issue 18, 2010, Pages 6244-6251

Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL HALIDES; ARYL IODIDES; CHEMO-SELECTIVITY; COUPLING PRODUCT; COUPLING REACTION; DIARYLALKYNES; GOOD YIELD; OPTIMIZED REACTION CONDITIONS; PROPIOLIC ACID; SONOGASHIRA COUPLING;

EID: 77956513822     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101398a     Document Type: Article
Times cited : (186)

References (70)
  • 1
    • 9644285669 scopus 로고
    • For original work, see:;;, For reviews on the Sonogashira reactions, see: Angew. Chem., Int. Ed. 2003, 42, 1566-1568
    • For original work, see: Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470 For reviews on the Sonogashira reactions, see: Tykwinski, R. P. Angew. Chem., Int. Ed. 2003, 42, 1566-1568
    • (1975) Tetrahedron Lett. , vol.16 , pp. 4467-4470
    • Sonogashira, K.1    Tohda, Y.2    Hagihara, N.3    Tykwinski, R.P.4
  • 54
    • 77956498968 scopus 로고    scopus 로고
    • note
    • We could not identify directly the intermediates 4 and 5 in the reaction mixture by GC and NMR because the two intermediates have acidic protons, which are difficult to detect in the basic conditions. Therefore, we treated the reaction mixture of Table 4 with the following procedure. The reaction mixture was reacted with MeI (1.0 mmol) and DBU (1.0 mmol) at room temperature for 3 h for the conversion of phenylpropiolic acid to methyl phenylpropiolate and treated with HCl etherate (1.0 mmol) for the acidification of phenylacetylene. These two compounds were detected in GC and NMR.
  • 55
    • 77956540710 scopus 로고    scopus 로고
    • note
    • We found similar results when 4-iodotoluene and phenyl bromide were employed as aryl halides instead of phenyl iodide and 4-bromotoluene.


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