Ligand-enabled meta-C-H activation using a transient mediator

Nature
Xiao-Chen WangJin-Quan Yu

Abstract

Achieving site selectivity in C-H functionalization reactions is a significant challenge, especially when the target C-H bond is distant from existing functional groups. Coordination of a functional group to a metal is often a key driving force and control element in many important reactions including asymmetric hydrogenation, epoxidation and lithiation. Exploitation of this effect has led to the development of a broad range of directed C-H activation reactions. However, these C-H activation methods are limited to proximal C-H bonds, which are spatially and geometrically accessible from the directing functional group. The development of meta-selective C-H functionalizations remains a significant challenge. We recently developed a U-shaped template that can be used to overcome this constraint and have shown that it can be used to selectively activate remote meta-C-H bonds. Although this approach has proved to be applicable to various substrates and catalytic transformations, the need for a covalently attached, complex template is a substantial drawback for synthetic applications. Here we report an alternative approach employing norbornene as a transient mediator to achieve meta-selective C-H activation with a simple and common o...Continue Reading

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Citations

Feb 20, 2016·Nature Chemistry·Alexandre VasseurIlan Marek
Jan 13, 2016·The Journal of Organic Chemistry·Mei-Juan ZhouLi Dang
Jan 28, 2016·Nature Communications·Shangda LiGang Li
Dec 29, 2015·Journal of the American Chemical Society·Youqing YangZhuangzhi Shi
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May 15, 2015·Organic Letters·He WangXingwei Li
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Feb 3, 2016·Chemistry : a European Journal·Kazuma AmaikeJunichiro Yamaguchi
Jan 13, 2016·Chemistry, an Asian Journal·Xiaogang LiuZhongfu An
Sep 4, 2015·Angewandte Chemie·Zhe DongGuangbin Dong
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Oct 20, 2015·Organic & Biomolecular Chemistry·Gang LiHankui Wu
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Aug 2, 2016·Angewandte Chemie·Ru-Yi ZhuJin-Quan Yu
Oct 22, 2016·Bioorganic & Medicinal Chemistry Letters·Eduardo J E Caro-DiazRobert M Jones
Oct 7, 2016·Chemical Communications : Chem Comm·Ying ZhaoAiwen Lei

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