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Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-08-17 , DOI: 10.1002/cjoc.202090091


Regioselective Csp3–H and Csp2–H alkynylation under Ir(III) and Ag(I) catalytic system was developed by judicious choice of readily available and structurally modifiable ketoximes and amides as the key substrates. Key features of this transformation included: 1) For ketoxime substrates, only primary Csp3–H at γ position to the nitrogen atom of ketoximes could readily undergo this Csp3–H alkynylation under Ir(III) catalysis. Notably, by slight modification of the structure of substrates, alcohols and ketones derived ketoximes could well participate in this transformation. 2) For amide substrates, primary phenylacetamides, which are challenging substrates due to the tautomerization of the distal O‐coordinating acetamides, could well serve as suitable substrates for the Csp2–H alkynylation. Significantly, when using oxidizing amides as the directing groups, α,β‐dehydrogenative C—H alkynylation was achieved. More details are discussed in the article by Shi et al. on page 929—934.
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中文翻译:

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Ir(III)和Ag(I)催化系统下的区域选择性Csp 3 -H和Csp 2 -H炔基化反应是通过明智地选择容易获得的和可在结构上修饰的酮肟和酰胺作为关键底物而开发的。该转化的关键特征包括:1)对于酮肟底物,只有在酮肟氮原子的γ位置的伯Csp 3 -H可以在Ir(III)催化下容易地进行Csp 3 -H烷基化。值得注意的是,通过稍微改变底物的结构,醇和酮衍生的酮肟可以很好地参与这种转化。2)对于酰胺类底物,伯苯基乙酰胺类由于远端O的互变异构化而成为具有挑战性的底物配位乙酰胺很适合用作Csp 2 -H炔基化反应的合适底物。明显地,当使用氧化酰胺作为指导基团时,实现了α,β-脱氢CHH炔基化。Shi等人的文章中讨论了更多细节。在929-934页上。
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更新日期:2020-08-24
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