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学科主题: 生命有机化学
题名: Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides
其他题名: 利用CuI/氨基酸催化的1-炔烃和烯基碘化物及2-溴三氟乙酸苯胺偶联进行的共轭烯炔和取代吲哚的组装
作者: Liu F(刘烽) ; Ma DW(马大为)
通讯作者: 马大为
刊名: J. Org. Chem.
发表日期: 2007
卷: 72, 期:13, 页:4844-4850
收录类别: SCI
部门归属: 上海有机所
英文摘要: Cross-coupling of 1-alkynes with vinyl iodides occurs at 80 degrees C 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 K2CO3 in DMF at 80 degrees C 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 NHCOCF3 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.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000247246100031
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/15547
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Liu F,Ma DW. Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides[J]. J. Org. Chem.,2007,72(13):4844-4850.
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