烯烃
立体选择性
异构化
烯烃纤维
电泳剂
卡宾
位阻效应
芳基
化学
有机合成
烯丙基重排
组合化学
催化作用
有机化学
烷基
作者
Chen-Fei Liu,Hongyu Wang,R. Torrence Martin,Haonan Zhao,Osvaldo Gutiérrez,Ming Joo Koh
出处
期刊:Nature Catalysis
[Springer Nature]
日期:2021-07-29
卷期号:4 (8): 674-683
被引量:30
标识
DOI:10.1038/s41929-021-00658-2
摘要
Despite tremendous efforts aimed at devising methods for stereoselective alkene synthesis, critical challenges are yet to be addressed. Direct access to a diverse range of 1-aryl(boryl)-1-methyl-functionalized tri- and tetrasubstituted trans alkenes, entities that are prevalent in many important molecules, through a catalytic manifold from readily available α-olefin substrates remains elusive. Here, we demonstrate that catalytic amounts of a non-precious N-heterocyclic carbene–Ni(I) complex in conjunction with a sterically bulky base promote site- and trans-selective union of monosubstituted olefins with a wide array of electrophilic reagents to deliver tri- and tetrasubstituted alkenes in up to 92% yield and >98% regio- and stereoselectivity. The protocol is amenable to the preparation of carbon- and heteroatom-substituted C=C bonds, providing distinct advantages over existing transformations. Utility is highlighted through concise stereoselective synthesis of biologically active compounds. Stereoselective synthesis of tri-and tetrasubstituted olefins is challenging due to the usually low energy difference between their E/Z isomers. Now, access to these molecules in high E:Z ratios from monosubstituted olefins is achieved through a sequential nickel-catalysed Heck reaction and alkene migration.
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