Copper(II)-Catalyzed C-N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol

被引：8
|
作者：
Du, Fangyu [1 ]
Zhou, Qifan [1 ]
Fu, Yang [1 ]
Chen, Yuanguang [1 ]
Wu, Ying [2 ]
Chen, Guoliang [1 ]
机构：
[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Liaoning, Peoples R China
[2] Yunnan Inst Trop Crops, Jinghong 666100, Peoples R China
来源：
SYNLETT | 2019年 / 30卷 / 19期
关键词：
N-arylation; quebrachitol; diethylene glycol; Cu(OAc)(2); Ullman coupling; AROMATIC-SUBSTITUTION; (HETERO)ARYL HALIDES; COPPER; LIGANDS; TAMIBAROTENE; AMIDATION; AMINATION; TACRINE; ANALOGS;
D O I：
10.1055/s-0039-1690707
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.
引用
收藏
页码：2161 / 2168
页数：8
相关论文
共 50 条
  • [31] Synthesis of N-alkyl-N′-aryl or Alkenylpiperazines: A Copper-Catalyzed C-N Cross-Coupling in the Presence of Aryl and Alkenyl Triflates and DABCO
    Ghazanfarpour-Darjani, Majid
    Barat-Seftejani, Forugh
    Khalaj, Mehdi
    Mousavi-Safavi, Seyed Mahmoud
    HELVETICA CHIMICA ACTA, 2017, 100 (08)
  • [32] Porous polymeric ligand promoted copper-catalyzed C-N coupling of(hetero)aryl chlorides under visible-light irradiation
    Erfei Wang
    Kaixuan Chen
    Yinan Chen
    Jiawei Zhang
    Xinrong Lin
    Mao Chen
    Science China(Chemistry), 2021, 64 (01) : 17 - 21
  • [33] Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation
    Erfei Wang
    Kaixuan Chen
    Yinan Chen
    Jiawei Zhang
    Xinrong Lin
    Mao Chen
    Science China Chemistry, 2021, 64 : 17 - 21
  • [34] Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation
    Wang, Erfei
    Chen, Kaixuan
    Chen, Yinan
    Zhang, Jiawei
    Lin, Xinrong
    Chen, Mao
    SCIENCE CHINA-CHEMISTRY, 2021, 64 (01) : 17 - 21
  • [35] Synthesis of N-1-aryl-purine nucleosides using copper-catalyzed C-N coupling of boronic acids
    Strouse, JJR
    Jeselnik, M
    Arterburn, JB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U187 - U187
  • [36] Photoinduced copper-catalyzed C-N coupling with trifluoromethylated arenes
    Huang, Jun
    Gao, Qi
    Zhong, Tao
    Chen, Shuai
    Lin, Wei
    Han, Jie
    Xie, Jin
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [37] Recent Progress in Copper-Catalyzed C-N Coupling Reactions
    Wang, Yefeng
    Zeng, Jinghui
    Cui, Xiaorui
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (02) : 181 - 199
  • [38] Copper-promoted C-N bond cross-coupling with phenylstannane
    Lam, PYS
    Vincent, G
    Bonne, D
    Clark, CG
    TETRAHEDRON LETTERS, 2002, 43 (16) : 3091 - 3094
  • [39] Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C-N coupling reaction of aryl halides and α-aminoamides
    Min, Xiangting
    Li, Xiaoyu
    Wang, Yu
    Dong, Yawen
    Tang, Jingjing
    Wang, Jing
    Liu, Jianhui
    TETRAHEDRON, 2018, 74 (21) : 2561 - 2566
  • [40] Potassium Carbonate Promoted C-N Coupling Reaction between Benzamides and Aryl Iodides
    Huang, Fei
    Wu, San
    Hu, Weiye
    Zhang, Songlin
    SYNTHESIS-STUTTGART, 2018, 50 (05): : 1090 - 1096
12345