Tuning of Regioselectivity in Inorganic Iodide-Catalyzed Alkylation of 2-Methoxyfurans via Electronic and Steric Effects
文献类型：期刊论文
| 作者 | Chen J(陈洁) ; Ni SJ(倪圣君) ; Ma SM(麻生明) |
| 刊名 | Adv. Synth. Catal.
 |
| 出版日期 | 2012 |
| 卷号 | 354期号:6页码:1114-1128 |
| ISSN号 | 1615-4150 |
| 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 |
| 通讯作者 | 麻生明 |
| 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. |
| 学科主题 | 金属有机化学 |
| 收录类别 | SCI |
| 原文出处 | http://dx.doi.org/10.1002/adsc.201100337 |
| 语种 | 英语 |
| WOS记录号 | WOS:000302936000021 |
| 公开日期 | 2013-08-22 |
| 源URL | [http://202.127.28.38/handle/331003/28001]  |
| 专题 | 上海有机化学研究所_金属有机化学国家重点实验室 |
| 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. |
入库方式： OAI收割
来源：上海有机化学研究所
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