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
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
  • [21] Silver-catalyzed [3+2+1] annulation of aryl amidines with benzyl isocyanide
    Lu, Xiaodong
    Xin, Xiaoyi
    Wan, Boshun
    TETRAHEDRON LETTERS, 2018, 59 (04) : 361 - 364
  • [22] Silver-catalyzed [3+2] cycloaddition of isocyanides with diazo compounds: new regioselective access to 1,4-disubstituted-1,2,3-triazoles
    Wang, Shuai
    Yang, Li-Jun
    Zeng, Jun-Liang
    Zheng, Yan
    Ma, Jun-An
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (11): : 1468 - 1474
  • [23] Palladium-Catalyzed Regioselective [3+2] Cycloadditions of α,β-Unsaturated Imines with Vinylethylene Carbonates: Access to Oxazolidines
    Wang, Yuanbo
    Wang, Yue
    Sun, Tong
    Liu, Qinglin
    Li, Er-Qing
    CATALYSTS, 2024, 14 (08)
  • [24] Silver-catalyzed [3+2]-cycloaddition of benzynes with diazocarbonyl species via a postulated (1H-indazol-1-yl)silver intermediate
    Wang, Chiou-Dong
    Liu, Rai-Shung
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (45) : 8948 - 8952
  • [25] Synthesis of Spirocyclic Pyrrolidine Compounds via Silver-Catalyzed Asymmetric [3+2] Cycloaddition Reaction of Imino Esters with α-Alkylidene Succinimides
    Inoue, Ayana
    Hosono, Kenya
    Furuya, Shohei
    Fukuzawa, Shin-ichi
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02): : 1249 - 1255
  • [26] Kinetic resolutions of azomethine imines via copper-catalyzed [3+2] cycloadditions
    Suárez, A
    Downey, CW
    Fu, GC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) : 11244 - 11245
  • [27] Trifluoromethylated 2,3-dihydro-1,3,4-thiadiazoles via the regioselective [3+2]-cycloadditions of fluorinated nitrile imines with aryl, hetaryl, and ferrocenyl thioketones
    Mloston, Grzegorz
    Urbaniak, Katarzyna
    Utecht, Greta
    Lentz, Dieter
    Jasinski, Marcin
    JOURNAL OF FLUORINE CHEMISTRY, 2016, 192 : 147 - 154
  • [28] Silver-Catalyzed [3+2] Cycloaddition for the Diastereoselective Synthesis of anti-3-Substituted Hydroindolin-2-Imines
    Yang, Zhongtao
    Luo, Xiai
    Zhang, Zhipeng
    Luo, Xiaoling
    Zheng, Jia
    Luo, Hui
    Yang, Weiguang
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4433 - 4439
  • [29] Silver-catalyzed [3+2] domino reaction: an efficient strategy to synthesize imidazole-5-carbaldehydes
    Wang, Changcheng
    Jiang, Hangqi
    Chen, Weifeng
    Dong, Jun
    Chen, Zhengwang
    Cao, Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (31) : 6463 - 6466
  • [30] From Rare Reagents to Rare Products: Regiospecific Silver-Catalyzed [3+2] Cycloaddition of Aryl-, Alkyl- and Aminosulfonyl Diazomethanes with Arenediazonium Tosylates
    Levashova, Ekaterina
    Bakulina, Olga
    Dar'in, Dmitry
    Bubyrev, Andrey
    Chuprun, Sergey
    Krasavin, Mikhail
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4239 - 4242