Vinylic Trifluoromethylselenolation via Pd-Catalyzed C-H Activation

被引:4
|
作者
de Zordo-Banliat, Arnaud [2 ]
Grollier, Kevin [1 ]
Vigier, Jordan [1 ]
Jeanneau, Erwann [3 ]
Dagousset, Guillaume [2 ]
Pegot, Bruce [2 ]
Magnier, Emmanuel [2 ]
Billard, Thierry [1 ]
机构
[1] Univ Lyon 1, Univ Lyon, Inst Chem & Biochem ICBMS UMR CNRS 5246, CNRS,CPE Lyon, 1 Rue Victor Grignard, F-69622 Lyon, France
[2] Univ Paris Saclay, Inst Lavoisier Versailles UMR CNRS 8180, CNRS, UVSQ, F-78035 Versailles, France
[3] Univ Lyon 1, Univ Lyon, Ctr Diffractometrie Henri Longchambon, 5 Rue Doua, F-69100 Villeurbanne, France
关键词
SELENIUM;
D O I
10.1002/chem.202202299
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Trifluorometylselenolation via C-H activation is barely described in literature. In particular, no such vinylic functionalization has been yet described. Herein, a palladiumcatalyzed trifluoromethylselenolation of vinylic C-H bonds is described. The 5-methoxy-8-aminoquinoline has been used as auxiliary directing group to perform this reaction. The reaction gives excellent yields with a-substituted compounds whatever the substituents and a microwave activation can be used to accelerate the reaction. With beta-substituted substrates lower yields, but still satisfactory, are obtained. This methodology was also successfully extended to other fluoroalkylselenyl groups.
引用
收藏
页数:5
相关论文
共 50 条
  • [11] Selective Halogenation of Arylurea Derivatives by Pd-Catalyzed C-H Activation
    Wang, Li
    Chen, Wenteng
    Shao, Zhanying
    Liu, Shen
    Yu, Yongping
    [J]. CURRENT ORGANIC CHEMISTRY, 2013, 17 (24) : 3092 - 3096
  • [12] Direct Allylic Functionalization Through Pd-Catalyzed C-H Activation
    Liron, Frederic
    Oble, Julie
    Lorion, Melanie M.
    Poli, Giovanni
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (27) : 5863 - 5883
  • [13] Pd-Catalyzed Directed Thiocyanation Reaction by C-H Bond Activation
    Gao, Melissa
    Chen, Mu-Yi
    Pannecoucke, Xavier
    Jubault, Philippe
    Besset, Tatiana
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (67) : 15497 - 15500
  • [14] Computational exploration of Pd-catalyzed C-H bond activation reactions
    Yang, Yun-Fang
    She, Yuanbin
    [J]. INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2018, 118 (21)
  • [15] Synthesis of cyclopropanes by Pd-catalyzed activation of alkyl C-H bonds
    Huang, Qinhua
    Larock, Richard C.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (52) : 7235 - 7238
  • [16] Domino Reactions Based on Pd-Catalyzed C-H Bond Activation
    Shen Jinhai
    Cheng Guolin
    Cui Xiuling
    [J]. PROGRESS IN CHEMISTRY, 2012, 24 (07) : 1324 - 1336
  • [17] Highly Efficient and Versatile Synthesis of Polyarylfluorenes via Pd-Catalyzed C-H Bond Activation
    Hwang, Seung Jun
    Kim, Hyun Jin
    Chang, Sukbok
    [J]. ORGANIC LETTERS, 2009, 11 (20) : 4588 - 4591
  • [18] Pd-catalyzed, nondirected C-H aminations
    Emmert, Marion H.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [19] Synthesis of substituted 2H-Chromenes via Pd-catalyzed C-H activation and thermal cyclization
    Maikhuri, Vipin K.
    Verma, Vineet
    Mathur, Divya
    Prasad, Ashok K.
    Khatri, Vinod
    [J]. CARBOHYDRATE RESEARCH, 2024, 536
  • [20] Pd-Catalyzed Direct C-H Activation for the C5-Olefination of Methyleneindolinones
    Xu, Xian-Kuan
    Liu, Jian-Wei
    Li, Deng-Yuan
    Liu, Pei-Nian
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (10): : 7288 - 7295