Aminolysis of Aryl Ester Using Tertiary Amine as Amino Donor via C-O and C-N Bond Activations

被引：68
|
作者：
Bao, Yong-Sheng [1 ]
Zhaorigetu, Bao [1 ]
Agula, Bao [1 ]
Baiyin, Menghe [1 ]
Jia, Meilin [1 ]
机构：
[1] Inner Mongolia Normal Univ, Inner Mongolia Key Lab Green Catalysis, Coll Chem & Environm Sci, Hohhot 010022, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 02期
关键词：
CATALYZED OXIDATIVE CYANATION; CROSS-COUPLING REACTIONS; ORGANOBORON COMPOUNDS; ALLYLIC ALKYLATIONS; MOLECULAR-OXYGEN; SODIUM-CYANIDE; CLEAVAGE; CARBOXYLATES; COMPLEXES; ALDEHYDES;
D O I：
10.1021/jo4023974
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An aminolysis reaction between various aryl esters and inert tertiary amines by C-O and C-N bond activations has been developed for the selective synthesis of a broad scope of tertiary amides under neutral and mild conditions. The mechanism may undergo the two key steps of oxidative addition of acyl C-O bond in parent ester and C-N bond cleavage of tertiary amine via an iminium-type intermediate.
引用
收藏
页码：803 / 808
页数：6
相关论文
共 50 条
  • [1] Aminolysis of Esters Using Quaternary Ammonium Salts as Amine Sources via Twice C-N Bond Activations
    Wang, Lili
    Li, Pengshuai
    Jia, Meilin
    Bao, Yongsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (05) : 1220 - 1230
  • [2] Energy-Efficient Green Catalysis: Supported Gold Nanoparticle-Catalyzed Aminolysis of Esters with Inert Tertiary Amines by C-O and C-N Bond Activations
    Bao, Yong-Sheng
    Baiyin, Menghe
    Agula, Bao
    Jia, Meilin
    Bao Zhaorigetu
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14): : 6715 - 6719
  • [3] Construction of C-C Bond via C-N and C-O Cleavage
    Pang, Xiaobo
    He, Rong-De
    Shu, Xing-Zhong
    SYNLETT, 2020, 31 (07) : 635 - 640
  • [4] Asymmetric synthesis via stereospecific C-N and C-O bond activation of alkyl amine and alcohol derivatives
    Pound, Sarah M.
    Watson, Mary P.
    CHEMICAL COMMUNICATIONS, 2018, 54 (87) : 12286 - 12301
  • [5] Benzyl C-O and C-N Bond Construction via C-C Bond Dissociation of Oxime Ester under Visible Light Irradiation
    Fan, Xiuwei
    Lei, Tao
    Liu, Zan
    Yang, Xiu-Long
    Cheng, Yuan-Yuan
    Liang, Ge
    Chen, Bin
    Tung, Chen-Ho
    Wu, Li-Zhu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1551 - 1558
  • [6] Cross-coupling polycondensation via C-O or C-N bond cleavage
    Yang, Ze-Kun
    Xu, Ning-Xin
    Takita, Ryo
    Muranaka, Atsuya
    Wang, Chao
    Uchiyama, Masanobu
    NATURE COMMUNICATIONS, 2018, 9
  • [7] π-Bond Dissociation Energies: C-C, C-N, and C-O
    Kass, Steven R.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (20): : 15158 - 15163
  • [8] Metal-free amino-controlled electrochemical intramolecular C-O and C-N couplings by site-selective activation of aryl C-N and C-O bonds
    Luo, Mu-Jia
    Lv, Gui-Fen
    Li, Yang
    Li, Jin-Heng
    GREEN CHEMISTRY, 2021, 23 (05) : 2044 - 2048
  • [9] Metal-free C-N bond-forming reaction: straightforward synthesis of anilines, through cleavage of aryl C-O bond and amide C-N bond
    Yu, Jianzhong
    Zhang, Peizhi
    Wu, Jun
    Shang, Zhicai
    TETRAHEDRON LETTERS, 2013, 54 (24) : 3167 - 3170
  • [10] Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations
    Wu, Jiamin
    Zhang, Jinli
    Jiao, Yongjuan
    Deng, Gongtao
    Li, Yingmei
    Zhang, Zhengyu
    Jiang, Yaojia
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17462 - 17470
12345