Construction of Difluoromethylated Tetrazoles via Silver-Catalyzed Regioselective [3+2] Cycloadditions of Aryl Diazonium Salts

被引：47
|
作者：
Peng, Xing [1 ,2 ]
Xiao, Ming-Yang [1 ,2 ]
Zeng, Jun-Liang [1 ,2 ]
Zhang, Fa-Guang [1 ,2 ]
Ma, Jun-An [1 ,2 ]
机构：
[1] Tianjin Univ, Dept Chem, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
[2] Tianjin Univ, Tianjin Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 12期
基金：
中国国家自然科学基金;
关键词：
MEDICINAL CHEMISTRY; FLUORINE;
D O I：
10.1021/acs.orglett.9b01697
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A silver-catalyzed regioselective [3 + 2] cycloaddition reaction of PhSO2CF2CHN2 with aryl diazonium salts is described. This protocol enables the straightforward construction of a novel class of difluoromethylated tetrazoles under mild conditions, tolerates a broad spectrum of functionalities, and is applicable to one-pot operation from commercially available aniline derivatives. The synthetic merit of this method is further demonstrated by the facile preparation of versatile difluoromethylated azoles, including a valuable HCF2-analogue of P2X3 receptor antagonist.
引用
收藏
页码：4808 / 4811
页数：4
相关论文
共 50 条
  • [1] Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts
    Xiao, Ming-Yang
    Chen, Zhen
    Zhang, Fa-Guang
    Ma, Jun-An
    TETRAHEDRON, 2020, 76 (14)
  • [2] Silver-Catalyzed [3+2] Cycloaddition Approach to Coumarin-Decorated Tetrazoles
    Liu, Xuan-Yu
    Zhai, Shi-Jing
    Feng, Fang-Fang
    Zhang, Fa-Guang
    Ma, Jun-An
    CHEMCATCHEM, 2020, 12 (22) : 5623 - 5626
  • [3] Silver-catalyzed regioselective [3+2] cycloaddition of arene-diazonium salts with 2,2,2-trifluorodiazoethane (CF3CHN2): a facile access to 2-aryl-5-trifluoromethyltetrazoles
    Chen, Zhen
    Fan, Shuang-Qing
    Zheng, Yan
    Ma, Jun-An
    CHEMICAL COMMUNICATIONS, 2015, 51 (92) : 16545 - 16548
  • [4] Silver-Catalyzed Stereoselective [3+2]Cycloadditions of Cyclopropyl-Indanimines with Carbonyl Compounds
    Hung, Hsiao-Hua
    Liao, Yi-Ching
    Liu, Rai-Shung
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (08) : 1545 - 1552
  • [5] Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes
    Jin, Cheng-An
    Liang, Ren-Xiao
    Jia, Yi-Xia
    SYNTHESIS-STUTTGART, 2024, 56 (20): : 3191 - 3198
  • [6] Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction
    Patouret, Remi
    Kamenecka, Theodore M.
    TETRAHEDRON LETTERS, 2016, 57 (14) : 1597 - 1599
  • [7] Silver-Catalyzed Asymmetric Desymmetrization of Cyclopentenediones via [3+2] Cycloaddition with α-Substituted Isocyanoacetates
    George, Jimil
    Kim, Hun Young
    Oh, Kyungsoo
    ORGANIC LETTERS, 2018, 20 (08) : 2249 - 2252
  • [8] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition
    Du, YS
    Lu, XY
    Yu, YH
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25): : 8901 - 8905
  • [9] Simultaneous Construction of C-N Axial and Central Chirality via Silver-Catalyzed Desymmetrizative [3+2] Cycloaddition of Prochiral N-Aryl Maleimides with Activated Isocyanides
    Zhang, Sen
    Luo, Zhang-Hong
    Wang, Wen-Tao
    Qian, Linghui
    Liao, Jia-Yu
    ORGANIC LETTERS, 2022, 24 (25) : 4645 - 4649
  • [10] [3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles
    Chuprun, Sergey
    Dar'in, Dmitry
    Kantin, Grigory
    Krasavin, Mikhail
    SYNTHESIS-STUTTGART, 2019, 51 (21): : 3998 - 4005
12345