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
	Liu F(刘烽) ; Ma DW(马大为)
刊名	J. Org. Chem.
	2007
卷号	72 期号:13 页码:4844-4850
ISSN号	0022-3263
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
通讯作者	马大为
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.
学科主题	生命有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo070547x
语种	英语
WOS记录号	WOS:000247246100031
公开日期	2013-02-19
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/15547]
专题	上海有机化学研究所_生命有机化学国家重点实验室
推荐引用方式 GB/T 7714	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.
APA	刘烽,&马大为.(2007).Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides.J. Org. Chem.,72(13),4844-4850.
MLA	刘烽,et al."Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides".J. Org. Chem. 72.13(2007):4844-4850.