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Iron‐Catalyzed Regioselective Alkenylboration of Olefins
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2020-10-14 , DOI: 10.1002/anie.202012607
Xiaolong Yu 1 , Hongling Zheng 1 , Haonan Zhao 1 , Boon Chong Lee 1 , Ming Joo Koh 1
Affiliation  

The first examples of an iron‐catalyzed three‐component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene‐containing substrates, ring cleavage leading to trisubstituted E‐alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

中文翻译:

铁催化的烯烃的区域选择性烯基硼化

公开了由双(频哪醇)二硼,链烯基卤化物(溴化物,氯化物或氟化物)和烯烃的区域选择性结合铁催化的三烯丙基硼酸酯的三组分合成的第一个例子。带有叔碳原子或季碳原子中心的产品可作为单一区域异构体以高达87%的产率生成,并完全保留了烯烃的立体化学。使用含环亚丙基的底物,可选择性地获得导致三取代的E-烯基硼酸酯的环裂解。机理研究揭示了与先前报道的烯烃碳硼化途径不同的反应属性。
更新日期:2020-10-14
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