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

被引：91
|
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
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 11期
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
下载
收藏
页码：2708 / 2711
页数：4
相关论文
共 50 条
  • [41] Organocatalytic Enantioselective Functionalization of Unactivated Indole C(sp3)-H Bonds
    Ma, Dengke
    Zhang, Zhihan
    Chen, Min
    Lin, Zhenyang
    Sun, Jianwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (44) : 15916 - 15921
  • [42] Catalytic C(sp3)-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ
    Xu, Yan
    Young, Michael C.
    Wang, Chengpeng
    Magness, David M.
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) : 9084 - 9087
  • [43] Palladium-catalysed C(sp3)-H arylation of primary amines using a catalytic alkyl acetal to form a transient directing group
    St John-Campbell, Sahra
    Ou, Alex
    Bull, James
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [44] 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
  • [45] Transient directing group controlled regiodivergent C(sp3)-H and C(sp2)-H polyfluoroalkoxylation of aromatic aldehydes
    Zhou, Jiayu
    Liu, Dan
    Bai, Chaolumen
    Bao, Agula
    Muschin, Tegshi
    Baiyin, Menghe
    Bao, Yong-Sheng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (21): : 5975 - 5981
  • [46] Transient directing group controlled regiodivergent C(sp3)-H and C(sp2)-H polyfluoroalkoxylation of aromatic aldehydes
    Zhou, Jiayu
    Liu, Dan
    Bai, Chaolumen
    Bao, Agula
    Muschin, Tegshi
    Baiyin, Menghe
    Bao, Yong-Sheng
    Organic Chemistry Frontiers, 2021, 8 (21) : 5975 - 5981
  • [47] Cp*RhIII-Catalyzed Arylation of C(sp3)-H Bonds
    Wang, Xiaoming
    Yu, Da-Gang
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (35) : 10280 - 10283
  • [48] Pd-catalyzed arylation of Sp3 C-H bonds
    Daugulis, Olafs
    Khan, Rana Kashif M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 132 - 132
  • [49] Photocatalytic (Het)arylation of C(sp3)-H Bonds with Carbon Nitride
    Das, Saikat
    Murugesan, Kathiravan
    Rodriguez, Gonzalo J. Villegas
    Kaur, Jaspreet
    Barham, Joshua P.
    Savateev, Aleksandr
    Antonietti, Markus
    Koenig, Burkhard
    ACS CATALYSIS, 2021, 11 (03) : 1593 - 1603
  • [50] Nickel-catalyzed chelation-assisted direct arylation of unactivated C(sp3)-H bonds with aryl halides
    Li, Mingliang
    Dong, Jiaxing
    Huang, Xiaolei
    Li, Kaizhi
    Wu, Qian
    Song, Feijie
    You, Jingsong
    CHEMICAL COMMUNICATIONS, 2014, 50 (30) : 3944 - 3946
12345