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Volumn , Issue 18, 2011, Pages 3361-3367

Pyridine N-oxide mediated oxidation of diarylalkynes with palladium on carbon

Author keywords

Alkynes; Heterogeneous catalysis; Nitrogen oxides; Oxidation; Palladium

Indexed keywords


EID: 79958716415     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001641     Document Type: Article
Times cited : (53)

References (75)
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    • oxidative amidation-diketonization of anilines with alkynes to α-ketoamides: b)
    • oxidative amidation-diketonization of anilines with alkynes to α-ketoamides: b) C. Zhang, N. Jiao, J. Am. Chem. Soc. 2010, 132, 28-29.
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    • The oxidations of some substrates 2 were completed using less than 5 equiv. of pyridine N-oxide
    • The oxidations of some substrates 2 were completed using less than 5 equiv. of pyridine N-oxide.
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    • Generation of pyridine was determined by 1H NMR spectroscopy after filtration of the reaction mixture
    • Generation of pyridine was determined by 1H NMR spectroscopy after filtration of the reaction mixture.
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    • Nitrogen-containing bases (e.g., pyridine, ammonia, or ammonium acetate) suppress the catalytic activity of Pd/C, see: a)
    • Nitrogen-containing bases (e.g., pyridine, ammonia, or ammonium acetate) suppress the catalytic activity of Pd/C, see: a) H. Sajiki, Tetrahedron Lett. 1995, 36, 3465-3468;
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    • Addition of acidic additives (e.g., MsOH) to quench pyridine could not improve the deacceleration effect of the reaction rate
    • Addition of acidic additives (e.g., MsOH) to quench pyridine could not improve the deacceleration effect of the reaction rate.
  • 66
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    • Typical procedure for the reuse of Pd/C is described in the Experimental Section
    • Typical procedure for the reuse of Pd/C is described in the Experimental Section.
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    • Substrates 2b-r were easily prepared by Sonogashira coupling between the arylalkynes and aryl halides, see: a)
    • Substrates 2b-r were easily prepared by Sonogashira coupling between the arylalkynes and aryl halides, see: a) H. Doucet, J.-C. Hierso, Angew. Chem. Int. Ed. 2007, 46, 834-871;
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    • Mono-or dialkylalkynes were not applicable to the present oxidation
    • Mono-or dialkylalkynes were not applicable to the present oxidation.
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    • [20] and was not generated in the present reaction of 2i bearing an ortho-alkynylanisole moiety, see: a)
    • [20] and was not generated in the present reaction of 2i bearing an ortho-alkynylanisole moiety, see: a) D. Yue, T. Yao, R. C. Larock, J. Org Chem. 2005, 70, 10292-10296;
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    • After completion of the oxidation, only filtration and extraction processes are required to obtain pure products 3a, 3e, 3m, 3n, 3q, and 3r. The case of 3a is depicted in the Experimental Section and Figure 4. Meanwhile, The yields of 3b, 3c, 3d, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3o, and 3p were determined after purification by silica gel column chromatography (n-hexane/EtOAc), because these products contained a slight amount of side products
    • After completion of the oxidation, only filtration and extraction processes are required to obtain pure products 3a, 3e, 3m, 3n, 3q, and 3r. The case of 3a is depicted in the Experimental Section and Figure 4. Meanwhile, The yields of 3b, 3c, 3d, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3o, and 3p were determined after purification by silica gel column chromatography (n-hexane/EtOAc), because these products contained a slight amount of side products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.