Synthesis of 2,3-dihydro-1H-indazoles by Rh( III)-catalyzed C-H cleavage of arylhydrazines

被引:16
|
作者
Yao, Jinzhong [1 ]
Feng, Ruokun [1 ]
Lin, Cong [1 ]
Liu, Zhanxiang [1 ]
Zhang, Yuhong [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
N BOND FORMATION; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; FUNCTIONALIZATION; HETEROCYCLES; INDAZOLES; ALKYNES; 1-ARYL-1H-INDAZOLES; CARBOXAMIDES; 1H-INDAZOLES;
D O I
10.1039/c4ob00921e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed efficient method for the synthesis of 2,3-dihydro-1H-indazoles is described. The reaction of arylhydrazines with olefins results in the corresponding 2,3-dihydro 1H-indazoles with exclusive regioselectivity via C-H bond activation. The utility of the methodology is illustrated by a rapid synthesis of 1H-indazoles under mild reaction conditions in half an hour.
引用
收藏
页码:5469 / 5476
页数:8
相关论文
共 50 条
  • [21] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Usama, Khan Mohammad
    Kanchupalli, Vinaykumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
  • [22] Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation
    Romanov-Michailidis, Fedor
    Sedillo, Kassandra F.
    Neely, Jamie M.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (28) : 8892 - 8895
  • [23] Rh(III)-catalyzed double C-H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
    Xu, Pan
    Wang, Guoqiang
    Wu, Zhongkai
    Li, Shuhua
    Zhu, Chengjian
    CHEMICAL SCIENCE, 2017, 8 (02) : 1303 - 1308
  • [24] Rh(III)-Catalyzed Synthesis of 2-Nitro-2H -azirines via sp3 C-H Activation
    Huang, Xiaojun
    Ge, Yun
    Qian, Yang
    Zhang, Zhengyu
    SYNLETT, 2022, 33 (10) : 969 - 972
  • [25] Iron(II)-catalyzed direct C-H cyanoalkylation of 2H-indazoles and coumarins via radical C-C bond cleavage
    Gao, Pin
    Cheng, Yuan-Bo
    Yang, Fan
    Guo, Li-Na
    Duan, Xin-Hua
    TETRAHEDRON LETTERS, 2019, 60 (35)
  • [26] Rh(III)-Catalyzed Atroposelective C-H Iodination of 1-Aryl Isoquinolines
    Zheng, Dong-Song
    Zhang, Wen-Wen
    Gu, Qing
    You, Shu-Li
    ACS CATALYSIS, 2023, 13 (08) : 5127 - 5134
  • [27] Rh(III)-Catalyzed Atroposelective C-H Selenylation of 1-Aryl Isoquinolines
    Zheng, Dong-Song
    Xie, Pei-Pei
    Zhao, Fangnuo
    Zheng, Chao
    Gu, Qing
    You, Shu-Li
    ACS CATALYSIS, 2024, 14 (08) : 6009 - 6015
  • [28] Rh(III)-Catalyzed Diverse C-H Functionalization of Iminopyridinium Ylides
    Dong, Zhenzhen
    Li, Pengfei
    Li, Xingwei
    Liu, Bingxian
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (09) : 2489 - 2494
  • [29] Organophotoredox-Catalyzed Direct C-H Amination of 2H-Indazoles with Amines
    Neogi, Sukanya
    Ghosh, Asim Kumar
    Majhi, Koushik
    Samanta, Sadhanendu
    Kibriya, Golam
    Hajra, Alakananda
    ORGANIC LETTERS, 2020, 22 (14) : 5605 - 5609
  • [30] Rh(III)-Catalyzed Trifluoromethylthiolation of Indoles via C-H Activation
    Wang, Qiang
    Xie, Fang
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 8361 - 8366