Copper-Catalyzed N-Arylation with Boronic Acid Pinacol Esters

被引:13
|
作者
Liu, Shuai [1 ]
Xu, Liang [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832003, Peoples R China
基金
中国国家自然科学基金;
关键词
N-arylation; C-N cross-coupling; Chelation assistance; boronic pinacol esters; CROSS-COUPLING REACTIONS; C-H AMIDATION; ROOM-TEMPERATURE; PALLADIUM; AMINATION; ARYL; ALKYNYLATION; ETHERS;
D O I
10.1002/ajoc.201800371
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed facile N-arylation of 2-acyl substituted anilines has been disclosed. Through chelation assistance of the weakly coordinating carbonyl groups, the Chan-Evans-Lam (CEL) C-N cross-coupling reactions proceeded at room temperature in open flasks. Furthermore, such chelation effects also enabled the direct utilization of aryl boronic acid pinacol esters in Cu-catalyzed CEL reactions under mild conditions.
引用
收藏
页码:1856 / 1863
页数:8
相关论文
共 50 条
  • [1] The copper-catalyzed N-arylation of indoles
    Antilla, JC
    Klapars, A
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11684 - 11688
  • [2] Copper-Catalyzed N-Arylation of Sulfonimidamides
    Azzaro, Stephane
    Desage-El Murr, Marine
    Fensterbank, Louis
    Lacote, Emmanuel
    Malacria, Max
    SYNLETT, 2011, (06) : 849 - 851
  • [3] Copper-catalyzed N-arylation of oxindoles
    Phillips, Dean P.
    Hudson, Andrew R.
    Nguyen, Bao
    Lau, Thomas L.
    McNeill, Matthew H.
    Dalgard, Jackline E.
    Chen, Jyun-Hung
    Penuliar, Richard J.
    Miller, Todd A.
    Zhi, Lin
    TETRAHEDRON LETTERS, 2006, 47 (40) : 7137 - 7138
  • [4] Copper-catalyzed N-arylation of Indoles
    Hisana, Kalathingal Nasreen
    Abdulla, Cheriya Mukkolakkol Afsina
    Anilkumar, Gopinathan
    CURRENT ORGANIC CHEMISTRY, 2022, 26 (09) : 857 - 886
  • [5] Copper-Catalyzed Trifluoromethylation of (Hetero)aryl Boronic Acid Pinacol Esters with YlideFluor
    Liu, Jing
    Xiao, Yisa
    Hao, Jian
    Shen, Qilong
    ORGANIC LETTERS, 2023, 25 (07) : 1204 - 1208
  • [6] A mild and efficient copper-catalyzed N-arylation of unprotected sulfonimidamides using boronic acids
    Battula, S. R. K.
    Subbareddy, G. V.
    Chakrayarthy, I. E.
    TETRAHEDRON LETTERS, 2014, 55 (02) : 517 - 520
  • [7] Copper-catalyzed N-arylation of pyrroles: an overview
    Hisana, Kalathingal Nasreen
    Afsina, C. M. A.
    Anilkumar, Gopinathan
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (37) : 17061 - 17076
  • [8] Copper-Catalyzed N-Arylation of Pyranoquinolinones with Boronic Acids at Room Temperature without Ligand
    Gao, Wei
    Gao, Fang
    Yang, Haikuan
    Wang, Zongde
    Huang, Yaru
    CATALYSTS, 2023, 13 (07)
  • [9] Copper-catalyzed N-arylation of imidazoles and benzimidazoles
    Altman, Ryan A.
    Koval, Erica D.
    Buchwald, Stephen L.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16): : 6190 - 6199
  • [10] Copper-Catalyzed N-Arylation of Indoles and Anilines with Aryltrialkoxysilanes
    Xie, Qi
    Zhang, Xiuqi
    Liu, Huijin
    Zhang, Fukuan
    Luo, Xuzhong
    Luo, Haiqing
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (03)