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Differentiation and functionalization of remote C-H bonds in adjacent positions.
Nature Chemistry ( IF 21.8 ) Pub Date : 2020-03-02 , DOI: 10.1038/s41557-020-0424-5
Hang Shi 1 , Yi Lu 1 , Jiang Weng 1 , Katherine L Bay 2 , Xiangyang Chen 2 , Keita Tanaka 1 , Pritha Verma 1 , Kendall N Houk 2 , Jin-Quan Yu 1
Affiliation  

Site-selective functionalization of C-H bonds will ultimately afford chemists transformative tools for editing and constructing complex molecular architectures. Towards this goal, it is essential to develop strategies to activate C-H bonds that are distal from a functional group. In this context, distinguishing remote C-H bonds on adjacent carbon atoms is an extraordinary challenge due to the lack of electronic or steric bias between the two positions. Herein, we report the design of a catalytic system leveraging a remote directing template and a transient norbornene mediator to selectively activate a previously inaccessible remote C-H bond that is one bond further away. The generality of this approach has been demonstrated with a range of heterocycles, including a complex anti-leukaemia agent and hydrocinnamic acid substrates.

中文翻译:

相邻位置的远程CH键的分化和功能化。

CH键的位点选择性官能化最终将为化学家提供用于编辑和构建复杂分子结构的转化工具。为了实现这一目标,至关重要的是要开发出激活功能团末端CH键的策略。在这种情况下,由于两个位置之间缺乏电子或位阻,因此区分相邻碳原子上的远程CH键是一个巨大的挑战。在本文中,我们报告了催化系统的设计,该催化系统利用远程指导模板和瞬态降冰片烯介体来选择性激活较远的一个键之前无法访问的远程CH键。这种方法的普遍性已通过一系列杂环得到了证明,其中包括复杂的抗白血病药和氢肉桂酸底物。
更新日期:2020-04-24
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