General Synthesis of Tri-Carbo-Substituted N2-Aryl-1,2,3-triazoles via Cu-Catalyzed Annulation of Azirines with Aryldiazonium Salts

被引：24

作者：

Feng, Fang-Fang ^{[1
,2
]}

Li, Jun-Kuan ^{[1
,2
]}

Liu, Xuan-Yu ^{[1
,2
]}

Zhang, Fa-Guang ^{[1
,2
,3
,4
]}

Cheung, Chi Wai ^{[1
,2
]}

Ma, Jun-An ^{[1
,2
,3
,4
]}

机构：

[1] Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Frontiers Sci Ctr Synthet Biol,Minist Educ, Tianjin 300072, Peoples R China

[2] Tianjin Univ, Tianjin Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China

[3] Natl Univ Singapore, Joint Sch, Fuzhou 350207, Peoples R China

[4] Tianjin Univ, Fuzhou 350207, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 16期

基金：

中国国家自然科学基金;

关键词：

OREXIN RECEPTOR ANTAGONIST; CLICK CHEMISTRY; EFFICIENT SYNTHESIS; CYCLOADDITION; AZIDE; TRIAZOLE; CONSTRUCTION; 2H-AZIRINES; DISCOVERY; METAL;

D O I：

10.1021/acs.joc.0c01433

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The general synthesis of fully substituted N-2-aryl-1,2,3-triazoles is hitherto challenging compared with that of the N-2-aryl counterparts. Herein, we describe a Cu-catalyzed annulation reaction of azirines and aryldiazonium salts. This regiospecific method allows access to a broad spectrum of tri-carbo N-2-aryl-1,2,3-triazoles substituted with diverse aryl and alkyl moieties. Its utility is highlighted by the synthesis of several triazole precursors applicable in drug discovery, as well as novel chiral binaphthyl ligands bearing triazole moieties.

引用

页码：10872 / 10883

页数：12

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