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1,1-二甲基-2,2,2-三氟乙基取代喹唑啉酮的无金属合成——喹唑啉-4(3)-酮与3,3,3-三氟-2,2-二甲基丙酸的串联自由基环化反应

Metal-free synthesis of 1,1-dimethyl-2,2,2-trifluoroethyl substituted quinazolinones tandem radical cyclization of quinazolin-4(3)-ones with 3,3,3-trifluoro-2,2-dimethylpropanoic acid.

作者信息

Gao Shenyuan, Cai Menglu, Wang Xiaozhong, Jiang Dapeng, Lin Pen, Dai Liyan

机构信息

Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, PR China.

出版信息

Org Biomol Chem. 2024 Aug 7;22(31):6376-6384. doi: 10.1039/d4ob00914b.

Abstract

A metal-free (NH)SO-mediated decarboxylative trifluoromethylation reaction of alkenes with 3,3,3-trifluoro-2,2-dimethylpropionic acid has been proposed. This method offers a novel route for the direct synthesis of a series of CMeCF-containing quinazolinones from basic chemical raw materials. The reaction mechanism was studied by a radical trapping test and DFT methods, verifying an oxidation-triggered cascade process promoted by the CMeCF radicals. This strategy provides advantages such as high yield, wide substrate compatibility, and high atom economy.

摘要

已提出一种无金属的(NH)SO介导的烯烃与3,3,3-三氟-2,2-二甲基丙酸的脱羧三氟甲基化反应。该方法为从基础化学原料直接合成一系列含CMeCF的喹唑啉酮提供了一条新途径。通过自由基捕获试验和密度泛函理论(DFT)方法研究了反应机理,证实了由CMeCF自由基促进的氧化引发的级联过程。该策略具有产率高、底物兼容性广和原子经济性高等优点。

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