Metal-Free One-Pot Synthesis of N,N′-Diarylamidines and N-Arylbenzimidazoles from Arenediazonium Salts, Nitriles, and Free Anilines

被引:31
作者
Youn, So Won [1 ]
Lee, Eun Mi
机构
[1] Hanyang Univ, Ctr New Direct Organ Synth, Dept Chem, Seoul 04763, South Korea
基金
新加坡国家研究基金会;
关键词
C-H AMINATION; DIAZONIUM SALTS; BENZIMIDAZOLE DERIVATIVES; IRIDIUM(III) COMPLEXES; PHENYL CATIONS; BOND FORMATION; LEAVING GROUP; AMIDINES; ARYLATION; CHEMISTRY;
D O I
10.1021/acs.orglett.6b02994
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient and facile metal-free, one-pot reaction has been developed to afford diversely substituted N-arylbenzimidazoles through chemoselective in situ generation of N,N'-diarylamidines from arenediazonium salts, nitrites, and free anilines. The advantages of this protocol consist of the operationally easy and simple one-pot procedure under metal-free and mild conditions, the direct use of inexpensive and commercially available chemicals, and thus, a cost-effective and greener process.
引用
收藏
页码:5728 / 5731
页数:4
相关论文
共 50 条
  • [41] Visible-light promoted one-pot synthesis of sulfonated spiro[4,5]trienones from propiolamides, anilines and sulfur dioxide under transition metal-free conditions
    Liu, Yu
    Wang, Qiao-Lin
    Chen, Zan
    Zhou, Quan
    Xiong, Bi-Quan
    Zhang, Pan-Liang
    Tang, Ke-Wen
    CHEMICAL COMMUNICATIONS, 2019, 55 (81) : 12212 - 12215
  • [42] Metal-free synthesis of N-sulfonylformamidines via skeletal reconstruction of sulfonyl oximonitriles
    Li, Feng
    Wu, Ziyan
    Wang, Jingjing
    Zhang, Siyuan
    Yu, Jiaxin
    Yuan, Zhen
    Liu, Jingya
    Shen, Renzeng
    Zhou, Yao
    Liu, Lantao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (03) : 627 - 632
  • [43] Synthesis of N,N′-Disulfonylamidines from Sulfonamides and Alkynes by a Two-Step, One-Pot Reaction with Nonafluorobutanesulfonyl Azide
    Ramon Suarez, Jose
    Kwiczak, Joanna
    Grenda, Katarzyna
    Luisa Jimeno, M.
    Luis Chiara, Jose
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (05) : 913 - 918
  • [44] Metal-free, visible-light-promoted oxidative radical cyclization of N-biarylglycine esters: one-pot construction of phenanthridine-6-carboxylates in water
    Natarajan, Palani
    Chuskit, Deachen
    Priya
    GREEN CHEMISTRY, 2019, 21 (16) : 4406 - 4411
  • [45] Transition metal-free steric controlled one-pot synthesis of highly substituted N-amino 1,2,3-triazole derivatives via diazo transfer reaction from β-keto esters
    Nagarajan, Rajendran
    Jayashankaran, Jayadevan
    Emmanuvel, Lourdusamy
    TETRAHEDRON LETTERS, 2016, 57 (24) : 2612 - 2615
  • [46] One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides
    Cioc, Razvan C.
    van der Niet, Daan J. H.
    Janssen, Elwin
    Ruijter, Eelco
    Orru, Romano V. A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (21) : 7808 - 7813
  • [47] Copper-Catalyzed One-Pot Synthesis of N,N-4-Triphenylthiazol-2-amines
    Weng, Jia-Hao
    Xu, Xiao-Hu
    Guan, Zhi-Peng
    Dong, Zhi-Bing
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (22) : 16390 - 16400
  • [48] Metal-Free, One-Pot Synthesis of Allylic and Benzylic Esters via Decarboxylation and C-H Bond Activation
    Mo, Hanjie
    Chen, Dingben
    Xu, Lingzhen
    Chen, Di
    Pan, Fuyou
    Yang, Jianguo
    SYNTHESIS-STUTTGART, 2015, 47 (02): : 209 - 215
  • [49] Metal-free trifunctionalization of phenylacetylenes: an efficient one-pot two-step synthesis of gem-bis(dithiocarbamates)
    Mondal, Manas
    Saha, Debajyoti
    Saha, Amit
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (29) : 5924 - 5928
  • [50] A Simple One-Pot and Transition Metal-free Synthesis of Diaryl- and Dialkyl Sulfides via Grignard Reaction/Deoxygenation
    Jung, Hee Seon
    Suh, Nuri
    Jeon, Heung Bae
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (05): : 779 - 782