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Efficient Assembly of Molecular Complexity Enabled by Palladium‐Catalyzed Heck Coupling/C(sp2)−H Activation/ C(sp3)−H Activation Cascade
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-07-03 , DOI: 10.1002/adsc.202000488
Chen He 1 , Wen‐Yong Han 1, 2 , Bao‐Dong Cui 1, 2 , Nan‐Wei Wan 1, 2 , Yong‐Zheng Chen 1, 2
Affiliation  

A palladium‐catalyzed [2+2+1] annulation among 3‐iodochromones, benzyl bromides, and norbornene has been developed. This annulation consists of a domino sequence involving Heck coupling/C(sp2)−H activation/C(sp3)−H activation, affording a variety of complex chromone derivatives bearing five contiguous tertiary carbon centers in up to 94% yield and 99:1 dr. Interestingly, the diastereoselectivity could be switched by fine‐tuning the solvent, in which endo isomer and exo isomer were obtained using mesitylene/CH3CN and mesitylene, respectively.

中文翻译:

钯催化的Heck偶联/ C(sp2)-H活化/ C(sp3)-H活化级联可实现分子复杂性的有效组装

在3-碘代色酮,苄基溴和降冰片烯中,钯催化了[2 + 2 + 1]环化反应。该环化过程由涉及Heck耦合/ C(sp 2)-H激活/ C(sp 3)-H激活的多米诺序列组成,提供了带有五个连续叔碳中心的多种复杂色酮衍生物,产率高达94%,99 :1博士 有趣的是,可以通过微调溶剂来改变非对映选择性,其中分别使用均三甲苯/ CH 3 CN和均三甲苯获得异构体和异构体。
更新日期:2020-09-05
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