Direct sulfonamidation of (hetero)aromatic C-H bonds with sulfonyl azides: a novel and efficient route toN-(hetero)aryl sulfonamides

被引:39
作者
Liu, Zhi [1 ]
Ebadi, Abdolghaffar [2 ]
Toughani, Mohsen [3 ]
Mert, Nihat [4 ]
Vessally, Esmail [3 ]
机构
[1] East China Jiaotong Univ, Sch Elect & Automat Engn, Nanchang 330013, Jiangxi, Peoples R China
[2] Islamic Azad Univ, Jouybar Branch, Dept Agr, Jouybar, Iran
[3] Islamic Azad Univ, Babol Branch, Dept Fishery, Babol, Iran
[4] Yuzuncu Yil Univ, Fac Vet Med, Dept Biochem, TR-65080 Van, Turkey
关键词
CATALYZED REGIOSELECTIVE AMIDATION; CROSS-COUPLING REACTIONS; CARBOXYLIC-ACIDS; N-ARYLATION; ARENES; DERIVATIVES; INDOLES; ACCESS; SULFAMIDATION; DELAVIRDINE;
D O I
10.1039/d0ra04255b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Aryl sulfonamides belong to a highly important class of organosulfur compounds which are found in a number of FDA-approved drugs such as dofetilide, dronedarone, ibutilide, sotalol, sulfadiazine, sulfamethizole, vemurafenib, and many more. There is therefore continuing interest in the development of novel and convenient protocols for the preparation of these pharmaceutically important compounds. Recently, direct sulfonamidation of (hetero)aromatic C-H bonds with easily available sulfonyl azides has emerged as an attractive and powerful strategy to accessN-(hetero)aryl sulfonamides where non-toxic nitrogen gas forms as the sole by-product. This review highlights recent advances and developments (2012-2020) in this fast growing research area with emphasis on the mechanistic features of the reactions.
引用
收藏
页码:37299 / 37313
页数:15
相关论文
共 94 条
  • [1] [Anonymous], 2017, J ORG CHEM
  • [2] N- Propargylamines: versatile building blocks in the construction of thiazole cores
    Arshadi, S.
    Vessally, E.
    Edjlali, L.
    Hosseinzadeh-Khanmiri, R.
    Ghorbani-Kalhor, E.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 625 - 638
  • [3] Cross-dehydrogenative coupling reactions between arenes (C-H) and carboxylic acids (O-H): a straightforward and environmentally benign access to O-aryl esters
    Arshadi, Sattar
    Banaei, Alireza
    Monfared, Aazam
    Ebrahimiasl, Saeideh
    Hosseinian, Akram
    [J]. RSC ADVANCES, 2019, 9 (30): : 17101 - 17118
  • [4] Recent developments in decarboxylative cross-coupling reactions between carboxylic acids and N-H compounds
    Arshadi, Sattar
    Ebrahimiasl, Saeideh
    Hosseinian, Akram
    Monfared, Aazam
    Vessally, Esmail
    [J]. RSC ADVANCES, 2019, 9 (16) : 8964 - 8976
  • [5] Synthetic Routes of Sulfonamide Derivatives: A Brief Review
    Ashfaq, Muhammad
    Shah, Syed Shoaib Ahmad
    Najjam, Tayyaba
    Shaheen, Salma
    Rivera, Gildardo
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2013, 10 (02) : 160 - 170
  • [6] Combination of sonochemical and freeze-drying methods for synthesis of graphene/Ag-doped TiO2 nanocomposite: A strategy to boost the photocatalytic performance via well distribution of nanoparticles between graphene sheets
    Ashraf, Muhammad Aqeel
    Liu, Zhenling
    Peng, Wan-Xi
    Jermsittiparsert, Kittisak
    Hosseinzadeh, Ghader
    Hosseinzadeh, Raza
    [J]. CERAMICS INTERNATIONAL, 2020, 46 (06) : 7446 - 7452
  • [7] Ruthenium catalyzed chemo and site-selective C-H amidation of oxobenzoxazine derivatives with sulfonyl azides
    Bakthadoss, Manickam
    Kumar, Polu Vijay
    Kumar, Ravan
    Surendar, Manickam
    Sharada, Duddu S.
    [J]. NEW JOURNAL OF CHEMISTRY, 2019, 43 (35) : 14190 - 14195
  • [8] Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
    Bhanuchandra, M.
    Yadav, M. Ramu
    Rit, Raja K.
    Kuram, Malleswara Rao
    Sahoo, Akhila K.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (45) : 5225 - 5227
  • [9] Iridium-Catalyzed Direct Regioselective C4-Amidation of Indoles under Mild Conditions
    Chen, Shuyou
    Feng, Boya
    Zheng, Xuesong
    Yin, Jiangliang
    Yang, Shiping
    You, Jingsong
    [J]. ORGANIC LETTERS, 2017, 19 (10) : 2502 - 2505
  • [10] Daghagheleh M., 2018, Chem. Rev. Lett. A, V1, P23, DOI DOI 10.22034/CRL.2018.85117