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学科主题: 金属有机化学
题名: Tuning of Regioselectivity in Inorganic Iodide-Catalyzed Alkylation of 2-Methoxyfurans via Electronic and Steric Effects
其他题名: 通过电子和位阻效应调控无机碘化物催化2-甲氧基呋喃烷基化反应中的区域选择性
作者: Chen J(陈洁) ; Ni SJ(倪圣君) ; Ma SM(麻生明)
通讯作者: 麻生明
刊名: Adv. Synth. Catal.
发表日期: 2012
卷: 354, 期:6, 页:1114-1128
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 华东师范大学
英文摘要: In the presence of inorganic iodide, the methoxy C?O bond in 2-methoxyfurans may be cleaved to afford the corresponding lactonic anion. Due to the presence of an electron-withdrawing group at the 3-position, the alkylation with normal organic iodides occurred at the 3-position highly regioselectively. However, when electron-deficient allylic iodides with an electron-withdrawing group at the 2-position were used the 5-alkylation products were formed as the major products with sodium iodide as the catalyst. With magnesium iodide as the catalyst, the 5-allylation occurred highly regioselectively. As a whole, the 3- vs. 5-alkylation selectivity may be determined by the relative steric hindrance at the 3- and 5-positions and the electronic effect of the allylic iodides. A rationale was proposed.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000302936000021
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28001
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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Recommended Citation:
Chen J,Ni SJ,Ma SM. Tuning of Regioselectivity in Inorganic Iodide-Catalyzed Alkylation of 2-Methoxyfurans via Electronic and Steric Effects[J]. Adv. Synth. Catal.,2012,354(6):1114-1128.
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