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Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-07-11 , DOI: 10.1002/anie.202005267
Manisha Swain 1 , Gusein Sadykhov 1 , Ruoxi Wang 1 , Ohyun Kwon 1
Affiliation  

The dealkenylative alkenylation of alkene C(sp3)−C(sp2) bonds has been an unexplored area for C−C bond formation. Herein 64 examples of β‐alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β‐nitrostyrenes by ozone/FeII‐mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso‐moracin and the drug (E)‐metanicotine.

中文翻译:


脱烯基化:烯烃的形式σ-键复分解。



烯烃 C(sp 3 )−C(sp 2 ) 键的脱烯基化烯基化一直是 C−C 键形成的未开发领域。本文报道了 64 个 β-烷基化苯乙烯衍生物的例子,这些衍生物是通过易于获得的原料烯烃与 β-硝基苯乙烯通过臭氧/Fe II介导的自由基取代反应合成的。这些反应在温和的反应条件下以良好的效率和高立体选择性进行,并且耐受一系列官能团。通过产品的多次合成转化以及天然产物异莫拉辛和药物 ( E )-间烟碱的合成,还证明了该策略的适用性。
更新日期:2020-07-11
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