Ruthenium(0)-Catalyzed sp3 C-H Bond Arylation of Benzylic Amines Using Arylboronates

被引:71
作者
Dastbaravardeh, Navid [1 ]
Schnuerch, Michael [1 ]
Mihovilovic, Marko D. [1 ]
机构
[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
基金
奥地利科学基金会;
关键词
ACTIVATION; FUNCTIONALIZATION; MECHANISM; PALLADIUM; AMIDES;
D O I
10.1021/ol300627p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ru-catalyzed direct arylation of benzylic sp(3) carbons of acyclic amines with arylboronates is reported. This highly regioselective and efficient transformation can be performed with various combinations of N-(2-pyridyl) substituted benzylamines and arylboronates. Substitution of the pyridine directing group in the 3-position proved to be crucial in order to achieve high arylation yields. Furthermore, the pyridine directing group can be removed in high yields via a two-step protocol.
引用
收藏
页码:1930 / 1933
页数:4
相关论文
共 50 条
  • [41] Iron- Catalyzed C( sp2)-H and C( sp3) -H Arylation by Triazole Assistance
    Gu, Qing
    Al Mamari, Hamad H.
    Graczyk, Karolina
    Diers, Emelyne
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) : 3868 - 3871
  • [42] Palladium-Catalyzed sp3 C-H Acetoxylation of α,α-Disubstituted α-Amino Acids
    Matsumura, Atsushi
    Usuki, Yoshinosuke
    Satoh, Tetsuya
    CHEMISTRY-SWITZERLAND, 2023, 5 (02): : 1369 - 1377
  • [43] Rhodium-Catalyzed C-H Bond Arylation of Arenes
    Bouffard, Jean
    Itami, Kenichiro
    C-H ACTIVATION, 2010, 292 : 231 - 280
  • [44] Unusual C-H Bond Activation and C(sp3)-C(sp3) Bond Formation at an Fe(II) Bis(amide) Carbene Complex
    Wong, Anthony
    Guevara, Kevin
    Wu, Guang
    Menard, Gabriel
    ORGANOMETALLICS, 2020, 39 (01) : 116 - 122
  • [45] An organic cation as a silver(I) analogue for the arylation of sp2 and sp3 C-H bonds with iodoarenes
    Arroniz, Carlos
    Denis, J. Gabriel
    Ironmonger, Alan
    Rassias, Gerasimos
    Larrosa, Igor
    CHEMICAL SCIENCE, 2014, 5 (09) : 3509 - 3514
  • [46] Palladium-catalyzed, aminoquinoline-directed arylation of phosphonamidate and phosphinic amide sp3 C-H bonds
    Tung Thanh Nguyen
    Daugulis, Olafs
    CHEMICAL COMMUNICATIONS, 2017, 53 (33) : 4609 - 4611
  • [47] Palladium-Catalyzed C(sp3)-H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group
    St John-Campbell, Sahra
    Ou, Alex K.
    Bull, James A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (67) : 17838 - 17843
  • [48] Palladium Catalyzed Arylation of C(sp3)-H Bonds of Carbonyl β-position in Water
    Luo Feihua
    Long Yang
    Li Zhengkai
    Zhou Xiangge
    ACTA CHIMICA SINICA, 2016, 74 (10) : 805 - 810
  • [49] Pd-Catalyzed γ-C(sp3)-H Fluorination of Free Amines
    Chen, Yan-Qiao
    Singh, Sukriti
    Wu, Yongwei
    Wang, Zhen
    Hao, Wei
    Verma, Pritha
    Qiao, Jennifer X.
    Sunoj, Raghavan B.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (22) : 9966 - 9974
  • [50] Palladium-catalyzed methylene C(sp3)-H arylation of the adamantyl scaffold
    Lao, Ye-Xing
    Wu, Jia-Qiang
    Chen, Yunyun
    Zhang, Shang-Shi
    Li, Qingjiang
    Wang, Honggen
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10): : 1374 - 1378