Al(OTf)3-Catalyzed Regioselective N2-Arylation of Tetrazoles with Diazo Compounds

被引：1
作者：
Zhou, Shuqi [1 ,2 ]
Li, Chunyan [1 ,2 ]
Zeng, Jie [2 ]
Lv, Jian [2 ]
Liao, Jie [3 ]
Wang, Haifeng [1 ,2 ,4 ]
Yan, Qiongjiao [2 ]
Gu, Shuangxi [1 ,2 ,4 ]
机构：
[1] Wuhan Inst Technol, Sch Chem Engn & Pharm, Wuhan 430205, Peoples R China
[2] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China
[3] Hubei Ind Technol Inst Dye Intermediates, Shishou 434400, Peoples R China
[4] Minist Educ, Key Lab Green Chem Engn Precess, Wuhan 430205, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 11期
基金：
中国国家自然科学基金;
关键词：
ARYL TETRAZOLES; INHIBITORS; DERIVATIVES; AZOLATION; DESIGN; AZOLES; ACIDS;
D O I：
10.1021/acs.joc.4c00531
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective methods to access alkylated tetrazoles still remain a challenging goal. Herein, we describe a novel regioselective protocol for N-2-arylation of tetrazoles with diazo compounds using inexpensive Al(OTf)(3). This reaction could be conducted under mild conditions to access a diverse array of alkylated tetrazoles with 2-substituted tetrazoles as the major products, demonstrating a comprehensive range of substrate compatibility and excellent functional group compatibility. Mechanistic studies revealed a carbene-free process in this reaction procedure. Furthermore, the scale-up reaction and transformations of the N-2-arylation of tetrazole products demonstrated the potential of this strategy.
引用
收藏
页码：7859 / 7864
页数：6
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