Rh-Catalyzed Direct Carboxylation of Alkenyl C-H Bonds of Alkenylpyrazoles

被引:15
|
作者
Saitou, Takanobu [1 ]
Jin, Yushu [1 ]
Isobe, Kotaro [1 ]
Suga, Takuya [1 ]
Takaya, Jun [1 ]
Iwasawa, Nobuharu [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, 2-12-1 O Okayama, Tokyo 1528551, Japan
关键词
carboxylation; alkenyl C-H activation; pyrazole; Rh(I) catalyst; TRANSITION-METAL-FREE; CARBON-DIOXIDE; MEDIATED CARBOXYLATION; CO2; PALLADIUM; CARBONYLATION; FUNCTIONALIZATION; ARYLPYRAZOLES; LACTONIZATION; ACTIVATION;
D O I
10.1002/asia.202000476
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Rh-catalyzed direct carboxylation of alkenyl C-H bonds was achieved by using pyrazole as a removable directing group. In the presence of 5 mol% RhCl3 . 3H(2)O, 6 mol% P(Mes)(3), and 2 equiv. of AlMe2(OMe), the alkenyl C-H bond of various alkenylpyrazoles was directly carboxylated in good yields under CO2 atmosphere. Furthermore, several useful transformations of the pyrazole moiety of the product were achieved to afford synthetically useful carboxylic acid derivatives in good yields.
引用
收藏
页码:1941 / 1944
页数:4
相关论文
共 50 条
  • [21] A Rh-catalyzed C-H insertion reaction for the oxidative conversion of carbamates to oxazolidinones
    Espino, CG
    Du Bois, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (03) : 598 - 600
  • [22] Palladium-Catalyzed Alkenyl C-H Bonds Benzoxylation of Benzofurans by Perester
    He, Li
    Xu, Yongjun
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (10)
  • [23] An Oxidative Approach to a Hydroxypiperidinone Utilizing a Rh-Catalyzed C-H Activation Process
    Ayers, Timothy A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (06) : 1415 - 1418
  • [24] Synthesis of Unprotected Spirocyclic β-Prolines and β-Homoprolines by Rh-Catalyzed C-H Insertion
    Espinosa, Miguel
    Noda, Hidetoshi
    Shibasaki, Masakatsu
    ORGANIC LETTERS, 2019, 21 (23) : 9296 - 9299
  • [25] Rh-Catalyzed Asymmetric C-H Activation for the Synthesis of Planar Chiral Ferrocenes
    Duan, Wei-Liang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (12) : 3598 - 3599
  • [26] Rh-catalyzed intramolecular sp2 C-H bond difluoromethylenation
    Li, Yajun
    Zhu, Jiangtao
    Xie, Haibo
    Li, Shan
    Peng, Dongjie
    Li, Zhengke
    Wu, Yongming
    Gong, Yuefa
    CHEMICAL COMMUNICATIONS, 2012, 48 (25) : 3136 - 3138
  • [27] Rh-catalyzed cyclization of diynes and enynes initiated by carbonyl-directed activation of aromatic and vinylic C-H bonds
    Tsuchikama, Kyoji
    Kuwata, Yusuke
    Tahara, Yu-Ki
    Yoshinami, Yusuke
    Shibata, Takanori
    ORGANIC LETTERS, 2007, 9 (16) : 3097 - 3099
  • [28] Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C-H Annulation and Their Application to Pd-Catalyzed Aerobic C-H Alkenylation
    Kim, Hyun Tae
    Kang, Eunsu
    Kim, Minkyu
    Joo, Jung Min
    ORGANIC LETTERS, 2021, 23 (09) : 3657 - 3662
  • [29] C-H functionalization of alkenyl SP2 C-H bonds
    Loh, Teck-Peng
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [30] Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes
    Potter, Tyler J.
    Kamber, David N.
    Mercado, Brandon Q.
    Ellman, Jonathan A.
    ACS CATALYSIS, 2017, 7 (01): : 150 - 153