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Volumn 130, Issue 3, 2008, Pages 833-835

Copper-catalyzed aerobic oxidative amidation of terminal alkynes: Efficient synthesis of ynamides

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; ALKYNE; CARBON; CHLORIDE; COPPER; HALIDE; NITROGEN; PHENYLACETYLENE; UNCLASSIFIED DRUG; YNAMIDE;

EID: 38349095933     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077406x     Document Type: Article
Times cited : (431)

References (56)
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    • de Meijere, A, Diederich, F, Eds, 2nd ed, Wiley-VCH: Chichester, and 2
    • de Meijere, A.; Diederich, F., Eds. Metal Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Chichester, 2004; Vol. 1 and 2.
    • (2004) Metal Catalyzed Cross-Coupling Reactions , vol.1
  • 2
    • 0345708168 scopus 로고    scopus 로고
    • For reviews and leading references to recent advances in copper-catalyzed coupling reactions, see: a
    • For reviews and leading references to recent advances in copper-catalyzed coupling reactions, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 5400-5449
    • Ley, S.V.1    Thomas, A.W.2
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    • (a) Stahl, S. S. Science 2005, 309, 1824-1826.
    • (2005) Science , vol.309 , pp. 1824-1826
    • Stahl, S.S.1
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    • (g) Zhang, Y. Tetrahedron 2006, 62, 3917-3927.
    • (2006) Tetrahedron , vol.62 , pp. 3917-3927
    • Zhang, Y.1
  • 36
    • 0028609943 scopus 로고    scopus 로고
    • Other stepwise methods for ynamide syntheses are known. For leading references, see the review articles in ref 6 and the following representative methods that employ alkynyliodonium salts: (a) Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255-1256.
    • Other stepwise methods for ynamide syntheses are known. For leading references, see the review articles in ref 6 and the following representative methods that employ alkynyliodonium salts: (a) Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255-1256.
  • 40
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    • (b) Hay, A. S. J. Org. Chem. 1962, 27, 3320-3321.
    • (1962) J. Org. Chem , vol.27 , pp. 3320-3321
    • Hay, A.S.1
  • 45
    • 33744786786 scopus 로고    scopus 로고
    • For a related reaction involving directed functionalization of aryl C-H bonds of 2-phenylpyridines, see: (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790-6791.
    • For a related reaction involving directed functionalization of aryl C-H bonds of 2-phenylpyridines, see: (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790-6791.
  • 47
    • 0043105154 scopus 로고    scopus 로고
    • The oxidative coupling of phenylacetylene and dimethylamine yields N,N-dimethyl-2-phenylethynylamine, which undergoes rapid hydrolysis to form N,N-dimethylphenylacetamide: Peterson, L. I. Tetrahedron Lett. 1968, 9, 5357-5360.
    • The oxidative coupling of phenylacetylene and dimethylamine yields N,N-dimethyl-2-phenylethynylamine, which undergoes rapid hydrolysis to form N,N-dimethylphenylacetamide: Peterson, L. I. Tetrahedron Lett. 1968, 9, 5357-5360.
  • 48
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    • An ynamide was obtained as an unexpected byproduct in the reaction between an alkynylcopper reagent and an iodoalkyl-substituted β-lactam. Balsamo, A, Macchia, B, Macchia, F, Rossello, A, Domiano, P. Tetrahedron Lett. 1985, 26, 4141-4144
    • An ynamide was obtained as an unexpected byproduct in the reaction between an alkynylcopper reagent and an iodoalkyl-substituted β-lactam. Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A.; Domiano, P. Tetrahedron Lett. 1985, 26, 4141-4144.
  • 52
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    • 2/DMSO reaction systems (stoichiometric and catalytic) is also presented in the Supporting Information
    • 2/DMSO reaction systems (stoichiometric and catalytic) is also presented in the Supporting Information
  • 53
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    • For examples of halogenation with copper halides, see: (a) Uemura, S, Okazaki, H, Okano, M, Sawada, S, Okada. A, Kuwabara, K. Bull. Chem. Soc. Jpn. 1978, 51, 1911-1912
    • For examples of halogenation with copper halides, see: (a) Uemura, S.; Okazaki, H.; Okano, M.; Sawada, S.; Okada. A.; Kuwabara, K. Bull. Chem. Soc. Jpn. 1978, 51, 1911-1912.
  • 56
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    • The nitrogen nucleophiles appear to be stable under the reaction conditions, and the unreacted nucleophile may be recovered from the reaction mixture, if desired. This point was successfully demonstrated in the 10 mmol scale preparation of ynamide 3f (Table 2), from which 90% recovery of the unreacted nucleophile was achieved. See Supporting Information for details.
    • The nitrogen nucleophiles appear to be stable under the reaction conditions, and the unreacted nucleophile may be recovered from the reaction mixture, if desired. This point was successfully demonstrated in the 10 mmol scale preparation of ynamide 3f (Table 2), from which 90% recovery of the unreacted nucleophile was achieved. See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.