Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp3)-H Bonds

被引:93
|
作者
Ma, Fei [1 ]
Lei, Min [2 ]
Hu, Lihong [1 ,2 ]
机构
[1] E China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China
[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
INTRAMOLECULAR AMINATION; POTENT INHIBITORS; ACTIVATION; DERIVATIVES; INDOLINES; OXIDATION; ALCOHOLS; RECEPTOR; KETONE;
D O I
10.1021/acs.orglett.6b01170
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward and efficient method has been developed for the synthesis of 2-benzylbenzaldehyde derivatives from 2-methylbenzaldehyde and iodobenzene via a C(sp(3))-H activation process. In the course of the activation reaction, acetohydrazone is formed between 2-benzylbenzaldehyde and acetohydrazine as a transient directing group. As a new kind of transient directing group, acetohydrazone exhibits a remarkable directing effect to give corresponding products in good to excellent yields.
引用
收藏
页码:2708 / 2711
页数:4
相关论文
共 50 条
  • [31] Rhodium-Catalyzed Intramolecular Silylation of Unactivated C(sp3)-H Bonds
    Kuninobu, Yoichiro
    Nakahara, Takahiro
    Takeshima, Hirotaka
    Takai, Kazuhiko
    ORGANIC LETTERS, 2013, 15 (02) : 426 - 428
  • [32] Palladium(II)-Catalyzed Directed Trifluoromethylthiolation of Unactivated C(sp3)-H Bonds
    Xiong, Heng-Ying
    Besset, Tatiana
    Cahard, Dominique
    Pannecoucke, Xavier
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) : 4204 - 4212
  • [33] Highly Regioselective Carbonylation of Unactivated C(sp3)-H Bonds by Ruthenium Carbonyl
    Hasegawa, Nao
    Charra, Valentine
    Inoue, Satoshi
    Fukumoto, Yoshiya
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) : 8070 - 8073
  • [34] Nickel-Catalyzed Site-Selective Amidation of Unactivated C(sp3)-H Bonds
    Wu, Xuesong
    Zhao, Yan
    Ge, Haibo
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (31) : 9530 - 9533
  • [35] PdII-Catalyzed Site-selectiveβ- andγ-C(sp3)-H Arylation of PrimaryAldehydes Controlled by Transient Directing Groups
    Li, Yi-Hao
    Ouyang, Yuxin
    Chekshin, Nikita
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (11) : 4727 - 4733
  • [36] 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
  • [37] Direct Arylation of α-Amino C(sp3)-H Bonds by Convergent Paired Electrolysis
    Ma, Yueyue
    Yao, Xiantong
    Zhang, Lei
    Ni, Pufan
    Cheng, Ruihua
    Ye, Jinxing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (46) : 16548 - 16552
  • [38] Catalytic alkane C-H functionalization by carbene insertion into unactivated C(sp3)-H bonds
    Pan, Yongzhen
    Wang, Yeming
    Karmakar, Swastik
    Sivaguru, Paramasivam
    Liu, Zhaohong
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (13): : 3777 - 3799
  • [39] Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C-H bonds utilizing amino acids as a directing group
    Cong, Zhanqing
    Gao, Feng
    Liu, Hong
    RSC ADVANCES, 2019, 9 (19) : 10820 - 10824
  • [40] The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis
    Cuthbertson, James D.
    MacMillan, David W. C.
    NATURE, 2015, 519 (7541) : 74 - 77