| SnCl2／Cu-Mediated Carbonyl Allylation Reaction in Water： Scope, Selectivity and Mechanism |
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| 引用本文： | 谭翔晖 侯永泉 刘磊 郭庆祥. SnCl2／Cu-Mediated Carbonyl Allylation Reaction in Water： Scope, Selectivity and Mechanism[J]. 中国化学, 2004, 22(5): 450-454. DOI: 10.1002/cjoc.20040220512 |
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| 作者姓名： | 谭翔晖 侯永泉 刘磊 郭庆祥 |
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| 作者单位： | DepartmentofChemistry,UniversityofScienceandTechnologyofChina,Hefei,Anhui230026,China |
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| 基金项目： | Project supported by Chinese Academy of Sciences (No. KJCXZ-SW-04) and the National Natural Science Foundation of China (No. 20332020). |
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| 摘 要： | Copper was found to be able to promote the SnC12-mediated carbonyl allylation reactions in water, giving the corresponding homoallylic alcohol products in very high yields. Detailed studies showed that the reaction could be applied to a variety of carbonyl compounds including those with hydroxyl, amino and nitro groups. It was also found that this reaction showed good regioselectivities for some substrates. Furthermore, carefully controled experiments and in situ NMR measurements provided important insights into the mechanism of the newly developed reaction.
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| 关 键 词： | 羰基烯丙基化反应 绿色化学 二氯化锡 铜 反应机理 水溶液 核磁共振 反应条件 |
SnCl_2/Cu-Mediated Carbonyl Allylation Reaction in Water: Scope, Selectivity and Mechanism |
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| TAN,Xiang-Hui HOU,Yong-Quan LIU,Lei GUO,Qing-Xiang. SnCl_2/Cu-Mediated Carbonyl Allylation Reaction in Water: Scope, Selectivity and Mechanism[J]. Chinese Journal of Chemistry, 2004, 22(5): 450-454. DOI: 10.1002/cjoc.20040220512 |
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| Authors: | TAN Xiang-Hui HOU Yong-Quan LIU Lei GUO Qing-Xiang |
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| Affiliation: | TAN,Xiang-Hui HOU,Yong-Quan LIU,Lei GUO,Qing-XiangDepartment of Chemistry,University of Science and Technology of China,Hefei,Anhui 230026,China |
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| Abstract: | Copper was found to be able to promote the SnCl2-mediated carbonyl allylation reactions in water, giving the corresponding homoallylic alcohol products in very high yields. Detailed studies showed that the reaction could be applied to a variety of carbonyl compounds including those with hydroxyl, amino and nitro groups. It was also found that this reaction showed good regioselectivities for some substrates. Furthermore, carefully controled ex-periments and in situ NMR measurements provided important insights into the mechanism of the newly developed reaction. |
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| Keywords: | carbonyl allylation Barbier reaction aqueous media green chemistry tin dichloride copper |
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