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
  • [31] Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant
    Rawat, Vishal Kumar
    Higashida, Kosuke
    Sawamura, Masaya
    SYNTHESIS-STUTTGART, 2021, 53 (18): : 3397 - 3403
  • [32] Nickel-catalyzed remote hydrosilylation of unconjugated enones with bulky triphenylsilane
    Chen, Xue
    Wang, Zhen
    Zhou, Jinyong
    Liu, Yunkui
    Jin, Hongwei
    Zhou, Bingwei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (37) : 8021 - 8024
  • [33] Nickel-catalyzed enantioselective reductive amination of benzylic ketones in alcohols
    Wang, Xiuhua
    Zhou, Jianrong Steve
    SCIENCE CHINA-CHEMISTRY, 2024, 67 (08) : 2566 - 2570
  • [34] A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents
    Li, Wei-Ze
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (23) : 5082 - 5086
  • [35] Nickel-Catalyzed Vinylation of Aryl Chlorides and Bromides with Vinyl ZnBr•MgBrCl
    Yamamoto, Tetsuya
    Yamakawa, Tetsu
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3603 - 3605
  • [36] Nickel-catalyzed decarboxylative coupling of an alkynyl carboxylic acid with aryl iodides
    Son, Yujeong
    Kim, Han-Sung
    Lee, Ju-Hyeon
    Jang, Jisun
    Lee, Chin-Fa
    Lee, Sunwoo
    TETRAHEDRON LETTERS, 2017, 58 (14) : 1413 - 1416
  • [37] Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes
    Ma, Teng
    Chen, Yate
    Li, Yuxiu
    Ping, Yuanyuan
    Kong, Wangqing
    ACS CATALYSIS, 2019, 9 (10): : 9127 - 9133
  • [38] Nickel-Catalyzed C(sp2)-C(sp3) Kumada Cross-Coupling of Aryl Tosylates with Alkyl Grignard Reagents
    Piontek, Aleksandra
    Ochedzan-Siodlak, Wioletta
    Bisz, Elwira
    Szostak, Michal
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (10) : 2329 - 2336
  • [39] Nickel-Catalyzed Enantioselective Pyridone C-H Functionalizations Enabled by a Bulky N-Heterocyclic Carbene Ligand
    Diesel, Johannes
    Finogenova, Anastasiia M.
    Cramer, Nicolai
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (13) : 4489 - 4493
  • [40] Nickel-catalyzed Asymmetric Propargylic Amination of Propargylic Carbonates with Aniline Derivatives
    Tsuji, Hiroaki
    Shimizu, Yuka
    Miyazaki, Yusuke
    Kawatsura, Motoi
    CHEMISTRY LETTERS, 2021, 50 (05) : 1002 - 1005