首页> 外文期刊>The Journal of Organic Chemistry >Assembly of Conjugated Enynes and Substituted Indoles via CuI/Amino Acid-Catalyzed Coupling of 1-Alkynes with Vinyl Iodides and 2-Bromotrifluoroacetanilides
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Assembly of Conjugated Enynes and Substituted Indoles via CuI/Amino Acid-Catalyzed Coupling of 1-Alkynes with Vinyl Iodides and 2-Bromotrifluoroacetanilides

机译:通过CuI /氨基酸催化的1-炔烃与乙烯基碘化物和2-溴三氟乙酰苯胺的偶联,组装共轭的炔烃和取代的吲哚

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摘要

Cross-coupling of 1-alkynes with vinyl iodides occurs at 80℃ in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol% of CuI, 6 mol% of L-proline, and K_2CO_3 in DMF at 80℃ leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF_3 enables the reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.
机译:在CuI / N,N-二甲基甘氨酸催化的二恶烷中,1-炔与乙烯基碘的交叉偶联发生在80℃,从而以良好或优异的收率得到共轭烯。在80℃下加热2-溴三氟乙酰苯胺,1-炔,2 mol%的CuI,6 mol%的L-脯氨酸和K_2CO_3的混合物在DMF中加热形成相应的吲哚。该转化涉及在芳基溴化物和1-炔烃之间的CuI / L-脯氨酸催化的偶联,然后是CuI介导的环化过程。由NHCOCF_3指导的邻位取代作用使反应在这些温和条件下进行。芳基乙炔和O-保护的炔丙醇都可以使用,从而以良好的产率产生5-,6-或7-取代的2-芳基和保护的2-羟甲基吲哚。但是,使用简单的脂族炔烃,收率较低。

著录项

  • 来源
    《The Journal of Organic Chemistry》 |2007年第13期|p.4844-4850|共7页
  • 作者

    Feng Liu; Dawei Ma;

  • 作者单位

    State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

  • 入库时间 2022-08-18 00:02:21

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