Semicarbazide: A Transient Directing Group for C(sp3)-H Arylation of 2-Methylbenzaldehydes

被引:24
|
作者
Wen, Fei [1 ]
Li, Zheng [1 ]
机构
[1] Northwest Normal Univ, Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
semicarbazide; transient directing group; 2-methylbenzaldehyde; 2-benzylbenzaldehyde; C-H ARYLATION; UNSYMMETRICAL ACRIDINES; AMINO AMIDE; BENZALDEHYDES; FUNCTIONALIZATION; ALDEHYDES; ALKYLATION; GAMMA-C(SP(3))-H; DERIVATIVES; CYCLIZATION;
D O I
10.1002/adsc.201901392
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Semicarbazide as an effective transient directing group for C(sp(3))-H arylation of 2-methylbenzaldehydes is described. Various substituted 2-benzylbenzaldehydes are efficiently synthesized by this strategy. The salient features of this protocol are the use of inexpensive transient directing group, wide scope of substrates with good functional group compatibility, up to 98% yield, and applicability to gram scale.
引用
收藏
页码:133 / 138
页数:6
相关论文
共 50 条
  • [21] Palladium-Catalyzed Arylation of C(sp2)-H Bonds and C(sp3)-H Bonds with 4-Amino-benzotriazole as the Bidentate Directing Group
    Li, Chengqian
    Wang, Zhuo
    Jin, Meina
    Song, Zhiguang
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (10) : 6966 - 6973
  • [22] The stabilizing effect of the transient imine directing group in the Pd(II)-catalyzed C(sp3)-H arylation of free primary amines
    Hu, Xiao-Xiao
    Liu, Jian-Biao
    Wang, Lu-Lin
    Huang, Fang
    Sun, Chuan-Zhi
    Chen, De-Zhan
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1670 - 1678
  • [23] Intramolecular palladium(ii)/(iv) catalysed C(sp3)-H arylation of tertiary aldehydes using a transient imine directing group
    St John-Campbell, Sahra
    Bull, James A.
    CHEMICAL COMMUNICATIONS, 2019, 55 (62) : 9172 - 9175
  • [24] Ligand-Promoted Palladium-Catalyzed β-C(sp 3 )-H Arylation of Ketones Using Acetohydrazide as a Transient Directing Group
    Jia, Kai
    Wang, Junjie
    Wang, Xuan
    Jiang, Chao
    SYNLETT, 2025, 36 (01) : 65 - 68
  • [25] Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp3)-H arylation
    Liu, Yunyun
    Zhang, Yi
    Cao, Xiaoji
    Wan, Jie-Ping
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 1122 - 1126
  • [26] Pd-Catalyzed sequential β-C(sp3)-H arylation and intramolecular amination of δ-C(sp2)-H bonds for synthesis of quinolinones via an N,O-bidentate directing group
    Guan, Mingyu
    Pang, Yubo
    Zhang, Jingyu
    Zhao, Yingsheng
    CHEMICAL COMMUNICATIONS, 2016, 52 (43) : 7043 - 7046
  • [27] Palladium-catalyzed enantioselective C(sp2)-H arylation of ferrocenyl ketones enabled by a chiral transient directing group
    Xu, Jiancong
    Liu, Yang
    Zhang, Jinling
    Xu, Xiaohua
    Jin, Zhong
    CHEMICAL COMMUNICATIONS, 2018, 54 (06) : 689 - 692
  • [28] 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
  • [29] Pd-Catalyzed β-C-H Arylation of Aldehydes and Ketones Based on a Transient Directing Group
    Wu, Liang-Fei
    Yao, Jian-Wei
    Zhang, Xin
    Liu, Si-Yuan
    Zhuang, Ze-Nian
    Wei, Kun
    ORGANIC LETTERS, 2021, 23 (16) : 6237 - 6241
  • [30] C(sp3)-H Bond Arylation and Amidation of Si-Bound Methyl Group via Directing Group Strategy
    Han, Jie-Lian
    Qin, Ying
    Zhao, Dongbing
    ACS CATALYSIS, 2019, 9 (07) : 6020 - +