Tetrabutylammonium Bromide-Promoted Metal-Free, Efficient, Rapid, and Scalable Synthesis of N-Aryl Amines

被引:9
|
作者
Johnson, Chad R. [1 ]
Ansari, Mohd Imran [1 ]
Coop, Andrew [1 ]
机构
[1] Univ Maryland, Sch Pharm, Dept Pharmaceut Sci, 20 N Pine St, Baltimore, MD 21201 USA
来源
ACS OMEGA | 2018年 / 3卷 / 09期
关键词
PALLADIUM-CATALYZED AMINATION; COUPLING REACTION; HALIDES; ALKYLATION; ARYLATION; LIGAND; HETEROARYL; PYRAZOLES; CHLORIDES; SCOPE;
D O I
10.1021/acsomega.8b01426
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rapid, transition metal-free, high-yielding, tetrabutylammonium bromide-promoted method of N-arylation is reported within. The optimized conditions tolerated a wide range of secondary amines and was equally effective with bromo-and chlorobenzene-including substituted aryl halides. The developed method is found to be effective for N-arylation when compared to earlier methods which involve harsh conditions, transition metals, lack of scalability, and long reaction times. Our method utilizes conventional heating only; it is readily scalable; and the products are facile to purify.
引用
收藏
页码:10886 / 10890
页数:5
相关论文
共 50 条
  • [1] A Metal-Free Synthesis of N-Aryl Carbamates under Ambient Conditions
    Guo, Wusheng
    Gonzalez-Fabra, Joan
    Bandeira, Nuno A. G.
    Bo, Carles
    Kleij, Arjan W.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (40) : 11686 - 11690
  • [2] Metal-Free Polychloromethylation/Cyclization of N-Aryl Acrylamides
    Sheng, Weijian
    Jin, Cheng'an
    Shan, Shang
    Jia, Yixia
    Gao, Jianrong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (02) : 325 - 329
  • [3] Metal-free efficient synthesis of aryl sulfonamides from N-hydroxy sulfonamide and amines
    Ramarao, E. V. Venkat Shivaji
    Solanke, Jayshree Nandkumar
    Chatterjee, Rana
    Gat, Savita
    Dhayalan, Vasudevan
    Dandela, Rambabu
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (29) : 5918 - 5923
  • [4] Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate
    Aithagani, Sravan Kumar
    Dara, Saidulu
    Munagala, Gurunadham
    Aruri, Hariprasad
    Yadav, Mahipal
    Sharma, Shweta
    Vishwakarma, Ram A.
    Singh, Parvinder Pal
    [J]. ORGANIC LETTERS, 2015, 17 (22) : 5547 - 5549
  • [5] Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides
    Liu, Zhaosheng
    Ji, Xiaochen
    Zhao, Feng
    Deng, Guojun
    Huang, Huawen
    [J]. CATALYSTS, 2023, 13 (06)
  • [6] Synthesis of N-Aryl Oxindole Nitrones through a Metal-Free Selective N-Arylation Process
    Wu, Si-Yi
    Ma, Xiao-Pan
    Liang, Cui
    Mo, Dong-Liang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06): : 3232 - 3238
  • [7] Metal-Free Arylalkylation of N-Aryl Acrylamides with Azobisalkyl-nitriles
    Tian, Qingshan
    He, Ping
    Kuang, Chunxiang
    [J]. SYNLETT, 2015, 26 (05) : 681 - 687
  • [8] Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation
    Tian, Long
    Zhang, Qianwei
    Ablajan, Keyume
    [J]. Synthesis (Germany), 2022, 54 (19) : 4353 - 4360
  • [9] Iodine-Promoted N-Acylation of Amines with Hydrazide: An Efficient Metal-Free Amidation
    Tian, Long
    Zhang, Qianwei
    Ablajan, Keyume
    [J]. SYNTHESIS-STUTTGART, 2022, 54 (19): : 4353 - 4360
  • [10] Transition metal-free, chemoselective arylation of thioamides yielding aryl thioimidates or N-aryl thioamides
    Villo, Piret
    Kervefors, Gabriella
    Olofsson, Berit
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (64) : 8810 - 8813