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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
Chen J(陈洁); Ni SJ(倪圣君); Ma SM(麻生明)
2012
发表期刊Adv. Synth. Catal.
ISSN1615-4150
卷号354期号:6页码:1114-1128
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.
学科领域金属有机化学
部门归属中科院上海有机化学研究所; 华东师范大学
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收录类别SCI
语种英语
WOS记录号WOS:000302936000021
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被引频次:5[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/28001
专题金属有机化学国家重点实验室
通讯作者Ma SM(麻生明)
推荐引用方式
GB/T 7714
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.
APA 陈洁,倪圣君,&麻生明.(2012).Tuning of Regioselectivity in Inorganic Iodide-Catalyzed Alkylation of 2-Methoxyfurans via Electronic and Steric Effects.Adv. Synth. Catal.,354(6),1114-1128.
MLA 陈洁,et al."Tuning of Regioselectivity in Inorganic Iodide-Catalyzed Alkylation of 2-Methoxyfurans via Electronic and Steric Effects".Adv. Synth. Catal. 354.6(2012):1114-1128.
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