Copper-Catalyzed Single C-H Amination of 8-Aminoquinoline-Directed Ferrocenes

被引:18
|
作者
Kanemoto, Kazuya [1 ]
Horikawa, Nao [1 ]
Hoshino, Shun [1 ]
Tokoro, Yuichiro [1 ,2 ]
Fukuzawa, Shin-Ichi [1 ]
机构
[1] Chuo Univ, Inst Sci & Engn, Dept Appl Chem, Tokyo 1128551, Japan
[2] Natl Def Acad Japan, Sch Appl Sci, Dept Appl Chem, 1-10-20 Hashirimizu, Yokosuka, Kanagawa 2398686, Japan
关键词
PLANAR CHIRAL FERROCENES; BOND FORMATION; AMIDATION; COMPLEXES; RECOGNITION; ARYLATION; LIGANDS; OXIDE; UNITS;
D O I
10.1021/acs.orglett.1c01294
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented copper-catalyzed C-H mono-amination of ferrocenes directed by an 8-aminoquinoline amide directing group is described. This reaction proceeds in the presence of a catalytic amount of copper catalyst with both cyclic and acyclic amines to afford the various aminoferrocenes. The C-H amination of ortho-substituted ferroceneamides was also achieved, enabling rapid access to multisubstituted ferrocenes that are useful for developing new functional molecules.
引用
收藏
页码:4966 / 4970
页数:5
相关论文
共 50 条
  • [1] Copper-Catalyzed 8-Aminoquinoline-Directed Selenylation of Arene and Heteroarene C-H Bonds
    Mandal, Anup
    Sahoo, Harekrishna
    Baidya, Mahiuddin
    ORGANIC LETTERS, 2016, 18 (13) : 3202 - 3205
  • [2] Copper-catalyzed monoselective C-H amination of ferrocenes with alkylamines
    Jia, Zhen-Sheng
    Yue, Qiang
    Li, Ya
    Xu, Xue-Tao
    Zhang, Kun
    Shi, Bing-Feng
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 : 2488 - 2495
  • [3] Copper-Catalyzed 8-Aminoquinoline-Directed Oxidative C-H/N-H Coupling for N-Arylation of Sulfoximines
    Grandhi, Gowri Sankar
    Dana, Suman
    Mandal, Anup
    Baidya, Mahiuddin
    ORGANIC LETTERS, 2020, 22 (07) : 2606 - 2610
  • [4] A General Method for Aminoquinoline-Directed, Copper-Catalyzed sp2 C-H Bond Amination
    Roane, James
    Daugulis, Olafs
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (13) : 4601 - 4607
  • [5] Copper-Catalyzed Intramolecular C-H Amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 908 - 911
  • [6] Directed copper-catalyzed dehydrogenative C-H amination of unsaturated sialic acids
    Li, Linlin
    Ferry, Angelique
    Messaoudi, Samir
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (02) : 466 - 471
  • [7] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752
  • [8] Copper-Catalyzed Aliphatic C-H Amination with an Amidine Moiety
    Chen, Hui
    Sanjaya, Stephen
    Wang, Yi-Feng
    Chiba, Shunsuke
    ORGANIC LETTERS, 2013, 15 (01) : 212 - 215
  • [9] Copper-Catalyzed Remote C-H Sulfonylation of 8-Aminoquinoline Amides with Arylsulfonyl Hydrazides
    Chen, Guoshu
    Zhang, Xuejian
    Zeng, Zihui
    Peng, Wanying
    Liang, Qiongzhi
    Liu, Jidan
    CHEMISTRYSELECT, 2017, 2 (05): : 1979 - 1982
  • [10] Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines
    Mei, Tian-Sheng (mei7900@sioc.ac.cn), 1600, American Chemical Society (140):