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Overcoming the limitations of directed C-H functionalizations of heterocycles
Alternative Title克服杂环碳氢键官能团化局限的新策略
Liu YJ(刘跃进)1; Xu H(徐辉)1; Kong WJ(孔维俊)1; Shang M(商明)1; Dai HX(戴辉雄)1; Yu JQ(余金权)1
Source PublicationNature
AbstractIn directed C-H activation reactions, any nitrogen or sulphur atoms present in heterocyclic substrates will coordinate strongly with metal catalysts. This coordination, which can lead to catalyst poisoning or C-H functionalization at an undesired position, limits the application of C-H activation reactions in heterocycle-based drug discovery(1-5), in which regard they have attracted much interest from pharmaceutical companies(3-5). Here we report a robust and synthetically useful method that overcomes the complications associated with performing C-H functionalization reactions on heterocycles. Our approach employs a simple N-methoxy amide group, which serves as both a directing group and an anionic ligand that promotes the in situ generation of the reactive PdX2 (X = ArCONOMe) species from a Pd(0) source using air as the sole oxidant. In this way, the PdX2 species is localized near the target C-H bond, avoiding interference from any nitrogen or sulphur atoms present in the heterocyclic substrates. This reaction overrides the conventional positional selectivity patterns observed with substrates containing strongly coordinating heteroatoms, including nitrogen, sulphur and phosphorus. Thus, this operationally simple aerobic reaction demonstrates that it is possible to bypass a fundamental limitation that has long plagued applications of directed C-H activation in medicinal chemistry.
Subject Area金属有机化学
Indexed BySCI
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Document Type期刊论文
Corresponding AuthorDai HX(戴辉雄); Yu JQ(余金权)
Recommended Citation
GB/T 7714
Liu YJ,Xu H,Kong WJ,et al. Overcoming the limitations of directed C-H functionalizations of heterocycles[J]. Nature,2014,515(7527):389-393.
APA 刘跃进,徐辉,孔维俊,商明,戴辉雄,&余金权.(2014).Overcoming the limitations of directed C-H functionalizations of heterocycles.Nature,515(7527),389-393.
MLA 刘跃进,et al."Overcoming the limitations of directed C-H functionalizations of heterocycles".Nature 515.7527(2014):389-393.
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