Rhodium(III)-Catalyzed Direct C-H Alkylation of 2-Aryl-1,2,3-triazole N-Oxides with Maleimides

被引：12
|
作者：
Zhao, Juanli [1 ]
Pi, Chao [1 ]
You, Chang [1 ]
Wang, Yong [1 ]
Cui, Xiuling [1 ]
Wu, Yangjie [1 ]
机构：
[1] Zhengzhou Univ, Dept Chem, Henan Key Lab Chem Biol & Organ Chem, Key Lab Appl Chem Henan Univ, 75 Daxue St, Zhengzhou 450052, Henan, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 48期
关键词：
Alkylation; High atom efficiency; Regioselectivity; Rhodium catalysis; UNACTIVATED C(SP(3))-H BONDS; CATALYZED DIRECT ALKYLATION; DIAZO-COMPOUNDS; CLICK CHEMISTRY; FUNCTIONALIZATION; CYCLIZATION; ACTIVATION; ARENES; DERIVATIVES; BENZAMIDES;
D O I：
10.1002/ejoc.201801353
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient rhodium(III)-catalyzed direct C-H ortho-alkylation of 2-aryl-1,2,3-triazole N-oxides has been developed using maleimides as the alkylation reagent. This protocol displays good functional group tolerance, high atom efficiency and avoids the external oxidant. Only mono-substituted products were obtained. Based on the results of deuterium exchange experiments, the N-oxide group plays an important role to improve the regioselectivity by increasing the steric hindrance.
引用
收藏
页码：6919 / 6923
页数：5
相关论文
共 50 条
  • [1] Iridium(III)-Catalyzed Direct C-H Sulfonamidation of 2-Aryl-1,2,3-triazole N-Oxides with Sulfonyl Azides
    Zhu, Bingfeng
    Cui, Xiuling
    Pi, Chao
    Chen, Dong
    Wu, Yangjie
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 326 - 332
  • [2] Copper-Catalyzed Direct Amination of 1,2,3-Triazole N-Oxides by C-H Activation and C-N Coupling
    Zhu, Jiayi
    Kong, Yubo
    Lin, Feng
    Wang, Baoshuang
    Chen, Zhengwang
    Liu, Liangxian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (07) : 1507 - 1515
  • [3] Rhodium-Catalyzed ortho-Cyanation of 2-Aryl-1,2,3-triazole: An Alternative Approach to Suvorexant
    Zhang, Hailong
    Jing, Li
    Zheng, Yang
    Sang, Rui
    Zhao, Yi
    Wang, Qiantao
    Wu, Yong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (06) : 723 - 729
  • [4] INFRARED SPECTRA OF 1,2,3-TRIAZOLE N-OXIDES
    BORELLO, E
    ZECCHINA, A
    GUGLIELMINOTTI, E
    JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (12): : 1243 - +
  • [5] Site-Selective Direct Arylation of 1,2,3-Triazole N-Oxides
    Liu, Wei
    Li, Yahui
    Wang, Yue
    Kuang, Chunxiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5272 - 5275
  • [6] NiSO4-catalyzed C-H activation/C-S cross-coupling of 1,2,3-triazole N-oxides with thiols
    Zhu, Jiayi
    Chen, Yu
    Lin, Feng
    Wang, Baoshuang
    Chen, Zhengwang
    Liu, Liangxian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) : 3711 - 3720
  • [7] Rh(III)-Catalyzed Selective C-H Alkylation and Alkenylation of 1,2,3-Benzotriazinones with Maleimides
    Xiao, Lin
    Shen, Dan-Ting
    Zou, Wen-Xuan
    Song, Jia-Lin
    Wei, Jiaohang
    Liu, Xiang
    Zhang, Shang-Shi
    Zhang, Luyong
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (17) : 3646 - 3652
  • [8] PHOTOCHEMISTRY OF AZOLE N-OXIDES .3. PHOTOINDUCED RING EXPANSION OF 2H-1,2,3-TRIAZOLE N-OXIDES
    GAINSFORD, GJ
    WOOLHOUSE, AD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1980, 33 (11) : 2447 - 2454
  • [9] Palladium-Catalyzed Olefination and Arylation of 2-Substituted 1,2,3-Triazole N-Oxides
    Liu, Wei
    Li, Yahui
    Xu, Bo
    Kuang, Chunxiang
    ORGANIC LETTERS, 2013, 15 (10) : 2342 - 2345
  • [10] Palladium-catalyzed highly regioselective oxidative homocoupling of 1,2,3-triazole N-oxides
    Peng, Xiangjun
    Huang, Panpan
    Jiang, Lili
    Zhu, Jiayi
    Liu, Liangxian
    TETRAHEDRON LETTERS, 2016, 57 (47) : 5223 - 5226
12345