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液相辅助研磨实现了镍催化、锰介导的苯并三嗪酮与苄基氯的脱氮交叉亲电偶联反应高效进行。

Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides.

作者信息

Zhang Xuanxuan, Hong Yingying, Zou Gang

机构信息

School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, China.

出版信息

Molecules. 2025 Feb 26;30(5):1060. doi: 10.3390/molecules30051060.

DOI:10.3390/molecules30051060
PMID:40076285
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11901950/
Abstract

An efficient and air-tolerant Ni-catalyzed denitrogenative cross-electrophile coupling of benzotriazinones with benzyl chlorides has been developed via liquid-assisted grinding by using Mn powders as reductant and DMF as assisting liquid in the presence of anhydrous calcium chloride. Scope and limitations of the protocol to access diarylmethanes have been demonstrated with more than 20 examples, showing acceptable tolerance to functional group and steric hindrance. Although electron-withdrawing substituents on benzotriazinone or benzyl counterparts decrease the yields significantly, a series of N-alkyl-2-benzylbenzamides, diarylmethanes bearing an ortho-carbamoyl aryl group, could be obtained in modest to good yields.

摘要

通过液体辅助研磨,在无水氯化钙存在下,以锰粉为还原剂、N,N-二甲基甲酰胺(DMF)为辅助液体,开发了一种高效且耐空气的镍催化苯并三嗪酮与苄基氯的脱氮交叉亲电偶联反应。该制备二芳基甲烷的方法的适用范围和局限性已通过20多个实例得到证明,对官能团和空间位阻具有可接受的耐受性。尽管苯并三嗪酮或苄基类似物上的吸电子取代基会显著降低产率,但一系列N-烷基-2-苄基苯甲酰胺,即带有邻甲酰氨基芳基的二芳基甲烷,仍可获得中等至良好的产率。

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Nickel-Catalyzed, Manganese-Assisted Denitrogenative Cross-Electrophile-Coupling of Benzotriazinones with Alkyl Halides for ortho-Alkylated Benzamides.镍催化、锰辅助的苯并三嗪酮与卤代烃的脱氮交叉亲电偶联反应合成邻烷基苯甲酰胺
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