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

被引：23
|
作者：
Wen, Fei [1 ]
Li, Zheng [1 ]
机构：
[1] Northwest Normal Univ, Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 01期
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
下载
收藏
页码：133 / 138
页数：6
相关论文
共 50 条
  • [31] Methylene C(sp3)-H β,β′-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand
    St John-Campbell, Sahra
    White, Andrew J. P.
    Bull, James A.
    ORGANIC LETTERS, 2020, 22 (05) : 1807 - 1812
  • [32] 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
  • [33] 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
  • [34] Transient Directing Group Enabled Pd-Catalyzed γ-C(sp3)-H Oxygenation of Alkyl Amines
    Chen, Yan-Quo
    Wu, Yongwei
    Wang, Zhen
    Qao, Jennifer X.
    Yu, Jin-Quan
    ACS CATALYSIS, 2020, 10 (10): : 5657 - 5662
  • [35] Stereoselective Palladium-Catalyzed C(sp3)-H Mono-Arylation of Piperidines and Tetrahydropyrans with a C(4) Directing Group
    Piticari, Amalia-Sofia
    Antermite, Daniele
    Higham, Joe, I
    Moore, J. Harry
    Webster, Matthew P.
    Bull, James A.
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (08) : 1488 - 1497
  • [36] Nano palladium catalyzed C(sp~3)—H bonds arylation by a transient directing strategy
    Jianxia Chen
    Chaolumen Bai
    Hongpeng Ma
    Dan Liu
    Yong-Sheng Bao
    Chinese Chemical Letters, 2021, 32 (01) : 465 - 469
  • [37] Borylation of Unactivated C(sp3)-H Bonds with Bromide as a Traceless Directing Group
    Zhang, Ge
    Li, Meng-Yao
    Ye, Wen-Bo
    He, Zhi-Tao
    Feng, Chen-Guo
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2021, 23 (08) : 2948 - 2953
  • [38] ortho-C(sp3)-H arylation of aromatic aldehydes using 2-amino-N-methyl-acetamide as a L,L-type transient directing group
    Wang, Jinyuan
    Liu, Yunzhi
    Han, Nan
    Gao, Yuan
    Luo, Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (09) : 1878 - 1882
  • [39] Buttressing Salicylaldehydes: A Multipurpose Directing Group for C(sp3)-H Bond Activation
    Yada, Akira
    Liao, Wenqing
    Sato, Yuta
    Murakami, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (04) : 1073 - 1076
  • [40] sp3 C-H bond arylation directed by amidine protecting group:: α-arylation of pyrrolidines and piperidines
    Pastine, Stefan J.
    Gribkov, Denis V.
    Sames, Dalibor
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) : 14220 - 14221
12345