Transition metal-free C-F/C-Cl/C-C cleavage of ClCF2COONa for the synthesis of heterocycles

被引：15

作者：

Yan, Yizhe ^{[1
]}

Cui, Chang ^{[1
]}

Wang, Jianyong ^{[2
]}

Li, Shaoqing ^{[1
]}

Tang, Lin ^{[3
]}

Liu, Yanqi ^{[1
]}

机构：

[1] Zhengzhou Univ Light Ind, Henan Key Lab Cold Chain Food Qual & Safety Contr, Henan Collaborat Innovat Ctr Food Prod & Safety, Sch Food & Biol Engn, Zhengzhou 450000, Henan, Peoples R China

[2] Qilu Univ Technol, Shandong Acad Sci, Sch Light Ind & Engn, Jinan 250353, Shandong, Peoples R China

[3] Xinyang Normal Univ, Coll Chem & Chem Engn, Xinyang 464000, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 35期

基金：

中国国家自然科学基金;

关键词：

IN-VITRO; 1,3,5-TRIAZINES; QUINAZOLINONES; DIFLUOROMETHYLATION; FUNCTIONALIZATION; COMPLEXES; AMINATION; METHANOL; CHLORIDE; DESIGN;

D O I：

10.1039/c9ob01641d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A transition metal-free and external oxidant-free annulation of substrates having two nitrogen-nucleophilic sites with ClCF2COONa was demonstrated, affording a series of 1,3,5-triazines and quinazolinones in up to 96% yields. Notably, ClCF2COONa was employed as the C1 synthon for valuable heterocycles. Using this protocol, two C-N bonds were formed in one pot via the cleavage of two C-F bonds, one C-Cl bond and one C-C bond. This method avoided the use of a transition metal and an oxidant and generated low toxicity inorganic waste.

引用

页码：8071 / 8074

页数：4

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