S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

被引：58

作者：

Deng, Shuilin ^{[1
]}

Chen, Haohua ^{[4
]}

Ma, Xingxing ^{[1
]}

Zhou, Yao ^{[1
]}

Yang, Kai ^{[2
]}

Lan, Yu ^{[4
,5
]}

Song, Qiuling ^{[1
,2
,3
]}

机构：

[1] Huaqiao Univ, Coll Mat Sci Engn, Coll Chem Engn, Inst Next Generat Matter Transformat, 668 Jimei Blvd, Xiamen 361021, Fujian, Peoples R China

[2] Fuzhou Univ, Coll Chem, Fuzhou 350108, Fujian, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[4] Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China

[5] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Henan, Peoples R China

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 28期

关键词：

ARYL BORONIC ACIDS; BIOLOGICAL EVALUATION; ELEMENTAL SULFUR; GEM-DIFLUOROOLEFINATION; OXIDATIVE CYCLIZATION; CHEMOTYPES DESIGN; DIAZO-COMPOUNDS; BOND; DIFLUOROALKYLATION; BENZOTHIAZOLES;

D O I：

10.1039/c9sc01333d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented S-8-catalyzed selective triple-cleavage of bromodifluoroacetamides is disclosed for the first time. Valuable 2-amido substituted benzimidazoles, benzoxazoles and benzothiazoles were obtained in good to excellent yields in a cascade protocol in this strategy. Mechanistic studies suggested that a C2 source was generated in situ by selective cleavage of three C-X bonds, including two inert C(sp(3))-F bonds on bromodifluoroacetamides, while leaving C-C bonds intact. This strategy will undoubtedly further consummate the role of halo difluoro compounds and enrich both fluorine chemistry and pharmaceutical sciences.

引用

页码：6828 / 6833

页数：6

共 51 条

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