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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
Shi M(施敏); Lu JM(陆建梅); Wei Y(魏音); Shao LX(邵黎雄)
2012
发表期刊Accounts Chem. Res.
ISSN0001-4842
卷号45期号:4页码:641-652
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.
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; 温州大学
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收录类别SCI
语种英语
WOS记录号WOS:000302838400016
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被引频次:121[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/331003/28003
专题金属有机化学国家重点实验室
通讯作者Shi M(施敏); Shao LX(邵黎雄)
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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.
APA 施敏,陆建梅,魏音,&邵黎雄.(2012).Rapid Generation of Molecular Complexity in the Lewis or Bronsted Acid-Mediated Reactions of Methylenecyclopropanes.Accounts Chem. Res.,45(4),641-652.
MLA 施敏,et al."Rapid Generation of Molecular Complexity in the Lewis or Bronsted Acid-Mediated Reactions of Methylenecyclopropanes".Accounts Chem. Res. 45.4(2012):641-652.
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