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
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
收藏
页码：133 / 138
页数：6
相关论文
共 50 条
  • [1] Cyclization by C(sp3)-H Arylation with a Transient Directing Group for the Diastereoselective Preparation of Indanes
    Provencher, Philip A.
    Bay, Katherine L.
    Hoskin, John F.
    Houk, K. N.
    Yu, Jin-Quan
    Sorensen, Erik J.
    ACS CATALYSIS, 2021, 11 (05) : 3115 - 3127
  • [2] Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)-H arylation
    Wen, Fei
    Li, Zheng
    SYNTHETIC COMMUNICATIONS, 2020, 50 (22) : 3462 - 3474
  • [3] PdII-Catalyzed ?-C(sp3)-H (Hetero)arylation of Ketones Enabled by Transient Directing Groups
    Li, Yi-Hao
    Ouyang, Yuxin
    Chekshin, Nikita
    Yu, Jin-Quan
    ACS CATALYSIS, 2022, 12 (17) : 10581 - 10586
  • [4] Methylene C(sp3)-H Arylation of Aliphatic Ketones Using a Transient Directing Group
    Hong, Kai
    Park, Hojoon
    Yu, Jin-Quan
    ACS CATALYSIS, 2017, 7 (10): : 6938 - 6941
  • [5] Palladium-Catalyzed β-C(sp3)-H Arylation of Aliphatic Ketones Enabled by a Transient Directing Group
    Wang, Yangyang
    Wu, Gaorong
    Xu, Xiaobo
    Pang, Binghan
    Liao, Shaowen
    Ji, Yafei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (10) : 7296 - 7303
  • [6] Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp3)-H Bonds
    Ma, Fei
    Lei, Min
    Hu, Lihong
    ORGANIC LETTERS, 2016, 18 (11) : 2708 - 2711
  • [7] 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
  • [8] PdII-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group
    Xiao, Li-Jun
    Hong, Kai
    Luo, Fan
    Hu, Liang
    Ewing, William R.
    Yeung, Kap-Sun
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (24) : 9594 - 9600
  • [9] Pd-Catalyzed C(sp3)-H Biarylation via Transient Directing Group Strategy
    Ding, Mingruo
    Hua, Wenkai
    Liu, Min
    Zhang, Fengzhi
    ORGANIC LETTERS, 2020, 22 (19) : 7419 - 7423
  • [10] Site-Selective γ-C(sp3)-H and γ-C(sp2)-H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group
    Lin, Hua
    Wang, Chao
    Bannister, Thomas D.
    Kamenecka, Theodore M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (38) : 9535 - 9541
12345