Acenaphthoimidazolium chloride-enabled nickel-catalyzed amination of bulky aryl tosylates

被引:26
|
作者
Jiang, Jian [1 ]
Zhu, Haibo [1 ]
Shen, Yajing [1 ]
Tu, Tao [1 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2014年 / 1卷 / 10期
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; HIGHLY-ACTIVE CATALYST; PALLADIUM COMPLEXES; SODIUM-BOROHYDRIDE; AGGREGATION; AMINES; RECOGNITION; ALKYLATION; ARYLAMINES; HALIDES;
D O I
10.1039/c4qo00233d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A robust catalyst derived from NiCl2 center dot(DME) and acenaphthoimidazolium chloride exhibited high activity towards the challenging amination of bulky and heterocyclic aryl tosylates with secondary amines under mild reaction conditions at 2 mol% catalyst loading within 3 hours. Further, a wide range of primary amines were also successfully mono-aminated by our newly developed protocol.
引用
收藏
页码:1172 / 1175
页数:4
相关论文
共 50 条
  • [21] Nickel-Catalyzed Decarboxylative Alkylation of Aryl Iodides with Anhydrides
    Chen, Hui
    Hu, Lu
    Ji, Wenzhi
    Yao, Licheng
    Liao, Xuebin
    ACS CATALYSIS, 2018, 8 (11): : 10479 - 10485
  • [22] Nickel-catalyzed intermolecular carboiodination of alkynes with aryl iodides
    Takahashi, Toshifumi
    Kuroda, Daiki
    Kuwano, Toru
    Yoshida, Yuji
    Kurahashi, Takuya
    Matsubara, Seijiro
    CHEMICAL COMMUNICATIONS, 2018, 54 (90) : 12750 - 12753
  • [23] Excited-State Nickel-Catalyzed Amination of Aryl Bromides: Synthesis of Diphenylamines and Primary Anilines
    Karpova, Lidia
    Daniel, Matej
    Kancherla, Rajesh
    Muralirajan, Krishnamoorthy
    Maity, Bholanath
    Rueping, Magnus
    ORGANIC LETTERS, 2024, 26 (08) : 1657 - 1661
  • [24] Nickel-catalyzed Buchwald-Hartwig amination of pyrimidin-2-yl tosylates with indole, benzimidazole and 1,2,4-triazole
    Gong, Hai-Peng
    Quan, Zheng-Jun
    Wang, Xi-Cun
    APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (11) : 949 - 953
  • [25] C(aryl)-O Activation of Aryl Carboxylates in Nickel-Catalyzed Biaryl Syntheses
    Goossen, Lukas J.
    Goossen, Kaethe
    Stanciu, Corneliu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) : 3569 - 3571
  • [26] Nickel-Catalyzed Electrosynthesis of Aryl and Vinyl Phosphinates
    Daili, Farah
    Ouarti, Abdelhakim
    Pinaud, Marine
    Kribii, Ibtihal
    Sengmany, Stephane
    Le Gall, Erwan
    Leonel, Eric
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (23) : 3452 - 3455
  • [27] Nickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates
    Kuriyama, Masami
    Kujirada, Shota
    Tsukuda, Kotaro
    Onomura, Osamu
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 1043 - 1048
  • [28] Nickel-Catalyzed Aminocarbonylation of Aryl Iodides with 1 atm CO
    Liu, Ning
    Wu, Xianqing
    Qu, Jingping
    Chen, Yifeng
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (01)
  • [29] Electroreductive Nickel-Catalyzed Allylation of Aryl Chlorides
    Fu, Xin
    Ran, Tingting
    Zhou, Yu
    Liu, Jie
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 6132 - 6139
  • [30] Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides
    Bai, Ya
    Liu, Nian
    Wang, Shutao
    Wang, Siyu
    Ning, Shulin
    Shi, Lingling
    Cui, Lili
    Zhang, Zhuoqi
    Xiang, Jinbao
    ORGANIC LETTERS, 2019, 21 (17) : 6835 - 6838