Synthesis of N-Aryl Amides by Ligand-Free Copper-Catalyzed ipso-Amidation of Arylboronic Acids with Nitriles

被引:10
|
作者
Qiao, Yan [1 ]
Li, Gaoqiang [1 ]
Liu, Sha [1 ]
Yangkai, Yujie [1 ]
Tu, Jingxuan [1 ]
Xu, Feng [1 ]
机构
[1] Shaanxi Normal Univ, Key Lab Macromol Sci Shaanxi Prov, Sch Chem & Chem Engn, Xian 710062, Shaanxi, Peoples R China
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 08期
基金
中国国家自然科学基金;
关键词
amides; nitriles; amination; copper catalysis; arylboronic acids; tandem reactions; COUPLING REACTION; BOND FORMATION; ARYLATION; AMINES; BENZOYLATION; REDUCTION; AMINATION; HALIDES;
D O I
10.1055/s-0036-1588373
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile copper-catalyzed ipso-amidation of arylboronic acids with nitriles has been developed. The method provides a highly efficient and economical synthesis of N-aryl amides with a broad substrate scope.
引用
收藏
页码:1834 / 1838
页数:5
相关论文
共 50 条
  • [1] Copper-Catalyzed Amidation of Arylboronic Acids with Nitriles
    Huang, He
    Jiang, Zhong-Tao
    Wu, Yang
    Gan, Cheng-Yan
    Li, Jin-Mei
    Xiang, Shi-Kai
    Feng, Chun
    Wang, Bi-Qin
    Yang, Wei-Te
    [J]. SYNLETT, 2016, 27 (06) : 951 - 955
  • [2] Ligand-free copper-catalyzed coupling of nitroarenes with arylboronic acids
    Zhang, Jilei
    Chen, Jiuxi
    Liu, Miaochang
    Zheng, Xingwang
    Ding, Jinchang
    Wu, Huayue
    [J]. GREEN CHEMISTRY, 2012, 14 (04) : 912 - 916
  • [3] Ligand-Free, Copper-Catalyzed Coupling Reaction of Aryl Aluminum Reagents with N-Aryl Thiosuccinimides
    Zhang, Zhihao
    Jia, Xiaoying
    Pu, Jiaxia
    Han, Lirong
    Hou, Jinsong
    Li, Qinghan
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2024, 21 (12) : 1055 - 1063
  • [4] Ligand-free copper-catalyzed direct amidation of diaryliodonium salts using nitriles as amidation reagents
    Cheng, Hui-cheng
    Zhou, Lichao
    Zhou, Xuming
    Ma, Jiao-li
    Guo, Penghu
    Zhang, Yang
    Ji, Hong-bing
    [J]. TETRAHEDRON LETTERS, 2021, 71
  • [5] Ipso-amidation of arylboronic acids: Xenon difluoride-nitriles as efficient reagent systems
    Prakash, G. K. Surya
    Moran, Matthew D.
    Mathew, Thomas
    Olah, George A.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (09) : 806 - 809
  • [6] Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water
    Yong, Fui-Fong
    Teo, Yong-Chua
    Chua, Guan-Leong
    Lim, Gina Shiyun
    Lin, Yizhen
    [J]. TETRAHEDRON LETTERS, 2011, 52 (11) : 1169 - 1172
  • [7] Copper-Catalyzed Regioselective Synthesis of N-Aryl Amides from Aldoximes and Aryl Halides
    Panda, Niranjan
    Mothkuri, Raghavender
    Nayak, Dinesh Kumar
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (08) : 1602 - 1605
  • [8] TBAB-promoted ligand-free copper-catalyzed cross-coupling reactions of aryl halides with arylboronic acids
    Li, Jin-Heng
    Li, Ji-Lan
    Xie, Ye-Xiang
    [J]. SYNTHESIS-STUTTGART, 2007, (07): : 984 - 988
  • [9] Copper-Catalyzed Carbonylative Cross-Coupling of Arylboronic Acids with N-Chloroamines for the Synthesis of Aryl Amides
    Yin, Zhiping
    Wang, Zechao
    Li, Wanfang
    Wu, Xiao-Feng
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (13) : 1769 - 1772
  • [10] Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids
    Cao, Ya-Nan
    Tian, Xin-Chuan
    Chen, Xing-Xiu
    Yao, Yun-Xin
    Gao, Feng
    Zhou, Xian-Li
    [J]. SYNLETT, 2017, 28 (05) : 601 - 606