Oxidative cross-coupling of pyridine N-oxides and ethers between C(sp2)-H/C(sp3)-H bonds under transition-metal-free conditions

被引：51
|
作者：
Sun, Wei [1 ]
Xie, Zuguang [1 ]
Liu, Jie [1 ]
Wang, Lei [1 ,2 ]
机构：
[1] Huaibei Normal Univ, Dept Chem, Huaibei 235000, Anhui, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 15期
基金：
美国国家科学基金会;
关键词：
C-H FUNCTIONALIZATION; DIRECT ARYLATION; ALKYLATION; AZOLES; AZINE; HETEROAROMATICS; DISCOVERY; ALCOHOLS; ADJACENT;
D O I：
10.1039/c5ob00237k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and efficient method based on the cross-coupling reactions of pyridine N-oxides with ethers between C(sp(2))-H/C(sp(3))-H bonds in the presence of TBHP was developed. The strategy provides an alternative approach to the pyridine moiety under transition-metal-free conditions.
引用
收藏
页码：4596 / 4604
页数：9
相关论文
共 50 条
  • [1] Rhodium(III)-Catalyzed Oxidative Cross-Coupling of Unreactive C(sp3)-H Bonds with C(sp2)-H Bonds
    Tan, Guangying
    You, Jingsong
    ORGANIC LETTERS, 2017, 19 (18) : 4782 - 4785
  • [2] Oxidative coupling between C(sp2)-H and C(sp3)-H bonds of indoles and cyclic ethers/cycloalkanes
    Yang, Qingjing
    Choy, Pui Ying
    Wu, Yinuo
    Fan, Baomin
    Kwong, Fuk Yee
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (09) : 2608 - 2612
  • [3] Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of sp3 and sp2 C-H Bonds
    Rathore, Vandana
    Sattar, Moh.
    Kumar, Raushan
    Kumar, Sangit
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9206 - 9218
  • [4] Cross-dehydrogenative coupling of α-C(sp3)-H of ethers/alkanes with C(sp2)-H of heteroarenes under metal-free conditions
    Ambala, Srinivas
    Thatikonda, Thanusha
    Sharma, Shweta
    Munagala, Gurunadham
    Yempalla, Kushalava Reddy
    Vishwakarma, Ram A.
    Singh, Parvinder Pal
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11341 - 11350
  • [5] Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp2)-H/C(sp3)-H Cross-Coupling
    Wen, Jiangwei
    Zhang, Fan
    Shi, Wenyan
    Lei, Aiwen
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (37) : 8814 - 8817
  • [6] Transition-Metal-Free Oxidative Cross-Coupling of Methylhetarenes with Imidazoheterocycles towards Efficient C(sp2)-H Carbonylation
    Sultana, Faria
    Shaik, Siddiq Pasha
    Alarifi, Abdullah
    Srivastava, Ajay Kumar
    Kamal, Ahmed
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 890 - 897
  • [7] Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp3)-H and C(sp2)-H Bonds
    Wu, Zhuo
    Wu, Zechen
    Sun, Xueliang
    Qi, Weixin
    Zhang, Zhengyang
    Zhang, Yanghui
    ORGANIC LETTERS, 2021, 23 (18) : 7161 - 7165
  • [8] Cross-Coupling Reactions between C(sp2)-H and C(sp3)-H Bonds via Sequential Dehydrogenation and C-H Insertion
    Kuninobu, Yoichiro
    Asanoma, Daisuke
    Takai, Kazuhiko
    SYNLETT, 2010, (19) : 2883 - 2886
  • [9] Electrochemical N(sp2)-H/C(sp3)-H cross-coupling reaction between sulfoximines and alkylarenes
    Zhu, Qing-Ru
    Zhang, Peng-Zhan
    Sun, Xiang
    Gao, Hui
    Wang, Pei-Long
    Li, Hongji
    GREEN CHEMISTRY, 2024, 26 (10) : 5824 - 5831
  • [10] Selectively Oxidative C(sp2)-H/C(sp3)-H Cross-Coupling of Benzamides with Amides by Nickel Catalysis
    Lv, Ningning
    Yu, Shuling
    Hong, Chao
    Han, De-Man
    Zhang, Yuhong
    ORGANIC LETTERS, 2020, 22 (23) : 9308 - 9312
12345