Iodine(III)-Mediated C-H Alkoxylation of Aniline Derivatives with Alcohols under Metal-Free Conditions

被引:20
|
作者
Jiang, Qing [1 ]
Wang, Jing-Yu [1 ]
Guo, Cancheng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, Adv Catalyt Engn Res Ctr, Minist Educ, Changsha 410082, Hunan, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 18期
基金
中国国家自然科学基金;
关键词
CATALYZED ORTHO-ALKOXYLATION; HYPERVALENT IODINE REAGENTS; CARBON BOND FORMATION; C=N BRIDGING GROUP; MULTICOMPONENT REACTIONS; UNACTIVATED METHYLENE; OXIDATIVE CLEAVAGE; POLYVALENT IODINE; ACID-DERIVATIVES; C-13; NMR;
D O I
10.1021/jo501601u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of a novel intermolecular oxidative C-H alkoxylation of aniline derivatives is described under metal-free conditions with high reaction rates at ambient temperature. In the presence of an I(III) oxidant, a range of aldehydes, anilines, and alcohol substrates undergo three-component coupling to produce synthetically useful alkoxyl-substituted N-arylimines. The preliminary mechanism investigations revealed that the transformation proceeds via imines as intermediates.
引用
收藏
页码:8768 / 8773
页数:6
相关论文
共 50 条
  • [41] Metal-Free C-H Functionalization of Alkanes by Aryldiazoacetates
    Tortoreto, Cecilia
    Rackl, Daniel
    Davies, Huw M. L.
    ORGANIC LETTERS, 2017, 19 (04) : 770 - 773
  • [42] Metal-Free Directed C-H Borylation of Pyrroles
    Wang, Zheng-Jun
    Chen, Xiangyang
    Wu, Lei
    Wong, Jonathan J.
    Liang, Yong
    Zhao, Yue
    Houk, Kendall N.
    Shi, Zhuangzhi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (15) : 8500 - 8504
  • [43] Metal-Free Catalytic Aromatic C-H Borylation
    Zhang, Hua
    Wang, Li
    SYNLETT, 2020, 31 (19) : 1857 - 1861
  • [44] Advances in the Transition Metal-Free C-H Trifluoromethylation
    Chen, Demao
    Jiang, Jianwen
    Wan, Jie-Ping
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (21) : 2582 - 2594
  • [45] Metal-Free ortho C-H Borylation of Thiobenzamides
    Lv, Jianxing
    Liang, Yixuan
    Ouyang, Yepeng
    Zhang, Hua
    ORGANIC LETTERS, 2024, 26 (18) : 3709 - 3714
  • [46] "Metal-free" electrooxidative C-H thiocyanation of arenes
    Kokorekin, V. A.
    Mel'nikova, E. I.
    Yaubasarova, R. R.
    Gorpinchenko, N. V.
    Petrosyan, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2019, 68 (11) : 2140 - 2141
  • [47] Metal-free C-H Borylation and Hydroboration of Indoles
    Nad, Pinaki
    Mukherjee, Arup
    ACS OMEGA, 2023, 8 (41): : 37623 - 37640
  • [48] Metal-Free C-H Amination for Indole Synthesis
    Jang, Young Ho
    Youn, So Won
    ORGANIC LETTERS, 2014, 16 (14) : 3720 - 3723
  • [49] Rhodium(III)-Catalyzed Oxidative C-H Alkylation of Aniline Derivatives with Allylic Alcohols To Produce β-Aryl Ketones
    Khake, Shrikant M.
    Chatani, Naoto
    ACS CATALYSIS, 2022, 12 (08) : 4394 - 4401
  • [50] Metal-free direct C-H phosphonation of N-heterocycles with diphenylphosphine oxides under mild conditions
    Cai, Zhao-Nan
    Han, Ya-Ping
    Zhang, Yuecheng
    Zhang, Hong-Yu
    Zhao, Jiquan
    Yang, Shang-Dong
    GREEN CHEMISTRY, 2023, 25 (14) : 5721 - 5726