化学
马尔科夫尼科夫法则
烯烃
烯烃纤维
碳阳离子
催化作用
芳香性
区域选择性
卤化
戒指(化学)
有机化学
组合化学
药物化学
分子
作者
Samantha A. Green,Suhelen Vásquez-Céspedes,Ryan A. Shenvi
摘要
Alkene hydroarylation forms carbon–carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel–Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.
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