Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation,The Journal of Organic Chemistry

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Hydrazine Hydrate Accelerates Neocuproine–Copper Complex Generation and Utilization in Alkyne Reduction, a Significant Supplement Method for Catalytic Hydrogenation
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-11-24 , DOI: 10.1021/acs.joc.1c01803
Yongsheng Zhang _{1,

2} , Jincheng Wang _{1,

3} , Zhenjiao Yang _{1,

2} , Zeng Zhang _{1,

3} , Xiaoyan He ₁ , Guoliang Chen ₂ , Gang Huang ₁ , Xiuhong Lu _{1,

3}

Affiliation

Diimine (HN═NH) is a strong reducing agent, but the efficiency of diimine oxidized from hydrazine hydrate or its derivatives is still not good enough. Herein, we report an in situ neocuproine–copper complex formation method. The redox potential of this complex enable it can serve as an ideal redox catalyst in the synthesis of diimine by oxidation of hydrazine hydrate, and we successfully applied this technique in the reduction of alkynes. This reduction method displays a broad functional group tolerance and substrate adaptability as well as the advantages of safety and high efficiency. Especially, nitro, benzyl, boc, and sulfur containing alkynes can be reduced to the corresponding alkanes directly, which provides a useful complementary method to traditional catalytic hydrogenation. Besides, we applied this method in the preparation of the Alzheimer’s disease drug CT-1812 and studied the mechanism.

中文翻译：

肼水合物加速新铜嘌呤-铜络合物的生成和在炔烃还原中的利用，这是催化加氢的重要补充方法

二亚胺（HN=NH）是一种强还原剂，但水合肼或其衍生物氧化二亚胺的效率仍然不够好。在此，我们报告了一种原位新铜素-铜络合物形成方法。该配合物的氧化还原电位使其可以作为一种理想的氧化还原催化剂用于水合肼氧化合成二亚胺，我们成功地将该技术应用于炔烃的还原。这种还原方法显示出广泛的官能团耐受性和底物适应性以及安全性和高效性的优点。特别是含硝基、苄基、boc和硫的炔烃可以直接还原为相应的烷烃，为传统的催化加氢提供了一种有用的补充方法。除了，

更新日期：2021-12-17

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