Palladium-catalyzed direct ortho C-O bond construction of azoxybenzenes with carboxylic acids and alcohols

被引:32
|
作者
Zhang, Duo [1 ]
Cui, Xiuling [1 ,2 ,3 ]
Yang, Fangfang [1 ]
Zhang, Qianqian [1 ]
Zhu, Yu [1 ]
Wu, Yangjie [1 ]
机构
[1] Zhengzhou Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, Zhengzhou 450052, Peoples R China
[2] Huaqiao Univ, Inst Mol Med, Sch Biomed Sci, Xiamen Key Lab Ocean & Gene Drugs, Xiamen 361021, Fujian, Peoples R China
[3] Chinese Educ Minist, Engn Res Ctr Mol Med, Xiamen 361021, Fujian, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2015年 / 2卷 / 08期
基金
中国国家自然科学基金;
关键词
AROMATIC AZO-COMPOUNDS; ORTHO-ACYLATION; ORTHO-ALKOXYLATION; H ACTIVATION; AZOBENZENES; AZOARENES; OXIDATION; FUNCTIONALIZATION; REACTIVITY; ARYLATION;
D O I
10.1039/c5qo00120j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd(II) catalyzed C-O bond formation of azoxybenzenes has been developed. An N-atom served as a directing group, as confirmed by the single crystal X-ray diffraction analysis of the palladium complex. The products were obtained in moderate to excellent yields for 29 examples. This protocol features high regioselectivity, wide functional group tolerance and atom economy.
引用
收藏
页码:951 / 955
页数:5
相关论文
共 50 条
  • [21] Palladium-Catalyzed Regioselective C-H Bond Acetoxylation-Alkoxylation of Azoxybenzenes
    Sun, Meng
    Zhang, Liang
    Hua, Cheng-Wen
    Wang, Zhe
    Hou, Le-Kai
    Cai, Su-Xian
    Li, Shuang
    [J]. SYNLETT, 2015, 26 (20) : 2843 - 2848
  • [22] Palladium-Catalyzed Direct ortho-Alkynylation of Aromatic Carboxylic Acid Derivatives
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 354 - 357
  • [23] Synthesis of oxygen heterocycles via a palladium-catalyzed C-O bond-forming reaction
    Palucki, M
    Wolfe, JP
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (42) : 10333 - 10334
  • [24] Access to Functionalized Indenes via Palladium-Catalyzed Homolytic Cleavage of a Furan C-O Bond
    Jiang, Kai
    Zeng, Guohui
    Xie, Xinyue
    Luo, Hui
    Fan, Qi
    Yin, Biaolin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2024,
  • [25] Palladium-Catalyzed Chemo- and Enantioselective C-O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis
    Chen, Jianzhong
    Zhang, Zhenfeng
    Liu, Delong
    Zhang, Wanbin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (29) : 8444 - 8447
  • [26] Palladium-Catalyzed Desulfitative Arylation by C-O Bond Cleavage of Aryl Inflates with Sodium Arylsulfinates
    Zhou, Chao
    Liu, Qingjiang
    Li, Yaming
    Zhang, Rong
    Fu, Xinmei
    Duan, Chunying
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10468 - 10472
  • [27] Palladium-catalyzed Suzuki-Miyaura cross-coupling of carboxylic-phosphoric anhydrides via C-O bond cleavage
    Ji, Haiyao
    Ma, Yilin
    Zhang, Jianwen
    Xing, Feifei
    Liu, Chengwei
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (27) : 5578 - 5584
  • [28] Palladium-Catalyzed Hydrolytic Cleavage of Aromatic C-O Bonds
    Wang, Meng
    Shi, Hui
    Camaioni, Donald M.
    Lercher, Johannes A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (08) : 2110 - 2114
  • [29] Palladium-catalyzed direct coupling reaction of propargylic alcohols with arylboronic acids
    Yoshida, M
    Gotou, T
    Ihara, M
    [J]. TETRAHEDRON LETTERS, 2004, 45 (29) : 5573 - 5575
  • [30] Palladium-Catalyzed Regioselective ortho-Acylation of Azoxybenzenes under Aqueous Conditions
    Chen, Xiaopei
    Ma, Zhiwei
    Wang, Chuanchuan
    Liu, Juntao
    Wu, Jinsong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) : 3176 - 3182