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
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 09期
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
  • [41] Copper-catalyzed N-arylation of carbamate-protected hydrazones with organobismuthanes
    Starkov, Pavel
    Zemskov, Ivan
    Sillard, Rannar
    Tsubrik, Olga
    Maeorg, Uno
    TETRAHEDRON LETTERS, 2007, 48 (07) : 1155 - 1157
  • [42] Copper-catalyzed direct oxidation and N-arylation of benzylamines with diaryliodonium salts
    LIU Xin
    MAO Dan
    WU ShengYing
    YU JianJun
    HONG Gang
    ZHAO Qiao
    WANG LiMin
    Science China(Chemistry), 2014, 57 (08) : 1 - 10
  • [43] Copper-catalyzed N-arylation of 2-arylindoles with aryl halides
    Wei Liu
    Li-Ya Han
    Rui-Li Liu
    Li-Ge Xu
    Yan-Lan Bi
    Chinese Chemical Letters, 2014, 25 (09) : 1240 - 1243
  • [44] Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines
    Gonela, Uma Maheshwar
    Ablordeppey, Seth Y.
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (07) : 2861 - 2864
  • [45] Efficient Copper-Catalyzed N-Arylation of Amides and Imidazoles with Aryl Iodides
    Ali, Md. Ashif
    Saha, Prasenjit
    Punniyamurthy, Tharmalingam
    SYNTHESIS-STUTTGART, 2010, (06): : 908 - 910
  • [46] Copper-Catalyzed Stepwise Aerobic Oxidation/N-Arylation from Benzothiazole
    Chen, Li
    Li, Xuezhen
    Xu, Keliang
    Xu, Qi
    Liu, Yan
    Liu, Ping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (01)
  • [47] Copper-Catalyzed N-Arylation of 2-Imidazolines with Aryl Iodides
    Davis, Owen A.
    Hughes, Matthew
    Bull, James A.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07): : 3470 - 3475
  • [48] Copper-catalyzed direct oxidation and N-arylation of benzylamines with diaryliodonium salts
    Xin Liu
    Dan Mao
    ShengYing Wu
    JianJun Yu
    Gang Hong
    Qiao Zhao
    LiMin Wang
    Science China Chemistry, 2014, 57 : 1132 - 1136
  • [49] Copper-Catalyzed N-Arylation of Hindered Substrates Under Mild Conditions
    Wentzel, Michael T.
    Hewgley, J. Brian
    Kamble, Rajesh M.
    Wall, Philip D.
    Kozlowski, Marisa C.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) : 931 - 937
  • [50] Copper-catalyzed direct oxidation and N-arylation of benzylamines with diaryliodonium salts
    Liu Xin
    Mao Dan
    Wu ShengYing
    Yu JianJun
    Hong Gang
    Zhao Qiao
    Wang LiMin
    SCIENCE CHINA-CHEMISTRY, 2014, 57 (08) : 1132 - 1136
12345