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Volumn 5, Issue 17, 2003, Pages 3057-3060

Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia

Author keywords

[No Author keywords available]

Indexed keywords

4 METHOXY 1 IODOBENZENE; ALKYNE; AMMONIA; BENZENE DERIVATIVE; KETONE DERIVATIVE; PALLADIUM COMPLEX; PHENYLETHYNE; UNCLASSIFIED DRUG;

EID: 0141743728     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035007a     Document Type: Article
Times cited : (176)

References (39)
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    • Recent studies on the improvement of Sonogashira coupling: (a) Herrmann. W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (c) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566.
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    • Recent studies on the improvement of Sonogashira coupling: (a) Herrmann. W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (c) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566.
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    • Recent studies on the improvement of Sonogashira coupling: (a) Herrmann. W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93. (b) Böhm, V. P. W.; Herrmann, W. A. Eur. J. Org. Chem. 2000, 3679. (c) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729. (d) Köllhofer, A.; Pullmann, T.; Plenio, H. Angew. Chem., Int. Ed. 2003, 42, 1056. (e) Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566.
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    • note
    • Addition of 2 mol % CuI to the reaction system of standard Sonogashira conditions with CO also resulted in noncarbonylative coupling to yield 70% of 4a and only 7% of 3a after stirring at room temperature for 4 h.
  • 39
    • 0141847859 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexanes/ethyl acetate (10/1) to give 85 mg of 1-(4-methoxyphenyl)-3-phenyl-2-propynone (72%).


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