Bulletin of the Korean Chemical Society

  • 제31권3호
  • /
  • Pages.570-576
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Radical Additions of Arenethiols to Ynamides for the Selective Synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides

  • Sato, Akinori (Department of Material Chemistry, Graduate School of Engineering, Kyoto University) ;
  • Yorimitsu, Hideki (Department of Material Chemistry, Graduate School of Engineering, Kyoto University) ;
  • Oshima, Koichiro (Department of Material Chemistry, Graduate School of Engineering, Kyoto University)
  • 발행 : 2010.03.20
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초록

A variety of ynamides undergo highly regio- and stereoselective radical addition of arenethiols with the aid of triethylborane as a radical initiator. The products, N-[(Z)-2-arylsulfanyl-1-alkenyl]amides, can be reduced with triethylsilane in trifluoroacetic acid to yield N-[2-(arylsulfanyl)alkyl]amides.

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  3. Thiol–yne coupling: revisiting old concepts as a breakthrough for up-to-date applications vol.10, pp.19, 2012, https://doi.org/10.1039/c2ob25217a
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  5. Thiyl Radicals in Organic Synthesis vol.114, pp.5, 2014, https://doi.org/10.1021/cr400441m
  6. Palladium-Catalyzed Addition of 1,3-Diones to Ynamides: An Entry to Alkoxy-Substituted Enamides vol.6, pp.9, 2014, https://doi.org/10.1002/cctc.201402398
  7. Palladium-Catalyzed Oxidative Sulfamidation: A Stereoselective Synthesis for Enesulfonamides vol.359, pp.4, 2017, https://doi.org/10.1002/adsc.201601048
  8. Rhodium-Catalyzed Annulation of Ynamides with Bifunctional Arylboron Reagents vol.12, pp.11, 2010, https://doi.org/10.1021/ol100769p
  9. ChemInform Abstract: Radical Additions of Arenethiols to Ynamides for the Selective Synthesis of N-[(Z)-2-(Arylsulfanyl)-1-alkenyl]amides. vol.41, pp.32, 2010, https://doi.org/10.1002/chin.201032094
  10. BEt3‐Initiated Thiol–Ene Click Reactions as a Versatile Tool To Modify Sensitive Substrates vol.2015, pp.36, 2010, https://doi.org/10.1002/ejoc.201500915
  11. Intermolecular Addition of Carbon-Centered Radicals to Ynamides. A Regio- and Stereoselective Route to Persubstituted α-Iodo-enamides vol.85, pp.6, 2010, https://doi.org/10.1021/acs.joc.9b03255
  12. Ynamides in Free Radical Reactions vol.362, pp.22, 2010, https://doi.org/10.1002/adsc.202000849