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
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
  • [21] Computational Studies on Rhodium(III) Catalyzed C-H Functionalization versus Deoxygenation of Quinoline N-Oxides with Diazo Compounds
    Deng, Chao
    Lam, Wai Han
    Lin, Zhenyang
    ORGANOMETALLICS, 2017, 36 (03) : 650 - 656
  • [22] Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation
    Chen, Xuan
    Zhu, Chongwei
    Cui, Xiuling
    Wu, Yangjie
    CHEMICAL COMMUNICATIONS, 2013, 49 (61) : 6900 - 6902
  • [23] Pd-catalyzed selective decarboxylation/C-H activation coupling of aryl acid with thiazole and oxazole directed by 1,2,3-triazole
    Ma, Xinyuan
    Liu, Yaowen
    Xie, Kai
    Jiang, Yubo
    TETRAHEDRON LETTERS, 2018, 59 (40) : 3624 - 3628
  • [24] Room-temperature oxidative Suzuki coupling reaction of 1,2,3-triazole N-oxides
    Liu, Wei
    Yu, Yanyan
    Fan, Boyi
    Kuang, Chunxiang
    TETRAHEDRON LETTERS, 2017, 58 (30) : 2969 - 2971
  • [25] Rhodium(III)-Catalyzed Direct C7-Selective Alkenylation and Alkylation of Indoles with Maleimides
    Sheng, Yaoguang
    Gao, Yi
    Duan, Bingbing
    Lv, Mengxia
    Chen, Yao
    Yang, Mengjie
    Zhou, Jianmin
    Liang, Guang
    Song, Zengqiang
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) : 307 - 313
  • [26] Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N-Oxides
    Roudesly, Fares
    Veiros, Luis F.
    Oble, Julie
    Poli, Giovanni
    ORGANIC LETTERS, 2018, 20 (08) : 2346 - 2350
  • [27] Cp*Rh(III)-Catalyzed C8 C-H Alkylation of Quinoline N-Oxides with Diazo Meldrum's Acid
    Huestis, Malcolm P.
    Leclerc, Jean-Philippe
    Larouche-Gauthier, Robin
    Aubert-Nicol, Samuel
    Yadav, Arun
    Sivamuthuraman, Koilpitchai
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (03) : 396 - 399
  • [28] Iodine-Catalyzed Direct C-H Alkenylation of Azaheterocycle N-Oxides with Alkenes
    Zhang, Zhenhao
    Pi, Chao
    Tong, Heng
    Cui, Xiuling
    Wu, Yongjie
    ORGANIC LETTERS, 2017, 19 (03) : 440 - 443
  • [29] Installation of Diverse Succinimides at C-8 Position of Quinoline N-Oxides via Rhodium(III)-Catalyzed C-H Functionalization
    Nale, Sagar D.
    Aslam, Mohammad
    Lee, Yong Rok
    CHEMISTRYSELECT, 2021, 6 (32): : 8244 - 8248
  • [30] Pd-catalyzed intramolecular C-H activation for the synthesis of fused-1,2,3-triazole quinolines and dihydroquinolines
    Ullah, Karim
    Allevi, Dario
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    Marrone, Federico
    Iazzetti, Antonia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (13) : 3143 - 3153