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学科主题: 金属有机化学
题名: Rapid Generation of Molecular Complexity in the Lewis or Bronsted Acid-Mediated Reactions of Methylenecyclopropanes
其他题名: 路易斯酸和质子酸催化的亚甲基环丙烷的反应-快速构建复杂分子
作者: Shi M(施敏) ; Lu JM(陆建梅) ; Wei Y(魏音) ; Shao LX(邵黎雄)
通讯作者: 施敏 ; 邵黎雄
刊名: Accounts Chem. Res.
发表日期: 2012
卷: 45, 期:4, 页:641-652
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 温州大学
英文摘要: Although they are highly strained, methylenecyclopropanes (MCPs) are readily accessible molecules that have served as useful building blocks in organic synthesis. MCPs can undergo a variety of ring-opening reactions because the release of cyclopropyl ring strain (40 kcal/mol) can provide a thermodynamic driving force for reactions and the pi-character of the bonds within the cyclopropane can afford the kinetic opportunity to initiate the ring-opening. Since the 1970s, the chemistry of MCPs has been widely explored in the presence of transition metal catalysts, but less attention had been paid to the Lewis or Bronsted acid mediated chemistry of MCPs. During the past decade, significant developments have also been made in the Lewis or Boosted acid mediated reactions of MCPs. This Account describes chemistry developed in our laboratory and by other researchers. Lewis and Bronsted adds can be used as catalysts or reagents in the reactions of MCPs with a variety of substrates, and substituents on the terminal methylene or on the cyclopropyl ring of MCPs significantly affect the reaction pathways. During the past decade, we and other researchers have found interesting transformations based on this chemistry. These new reactions include the ring expansion of MCPs, cycloaddition reactions of MCPs with aldehydes and imines, cycloaddition reactions of MCPs with nitriles in the presence of strong Bronsted acid, radical reactions of MCPs with 1,3-dicarbonyl compounds, intramolecular Friedel-Crafts reactions of MCPs with arenes, acylation reactions of MCPs, and the reaction of MCPs with 1,1,3-triarylprop-2-yn-1-ols or their methyl ethers. These Lewis or Bronsted acid mediated reactions of MCPs can produce a variety of new compounds such as cyclobutanones, indenes, tetrahydrofurans, and tetrahydroquinolines. Finally, we have also carried out computational studies to explain the mechanism of the Bronsted acid mediated reactions of MCPs with acetonitrile.
语种: 英语
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WOS记录号: WOS:000302838400016
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28003
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:
Shi M,Lu JM,Wei Y,et al. Rapid Generation of Molecular Complexity in the Lewis or Bronsted Acid-Mediated Reactions of Methylenecyclopropanes[J]. Accounts Chem. Res.,2012,45(4):641-652.
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