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
  • [31] Palladium-catalyzed benzylic C(sp3)-H arylation of o-alkylbenzaldehydes
    Lei, Lan
    Wu, Ping
    Liu, Zhuqing
    Lou, Jiang
    TETRAHEDRON LETTERS, 2021, 67
  • [32] 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
  • [33] Allylic C(sp3)-H arylation of olefins via ternary catalysis
    Huang, Huan-Ming
    Bellotti, Peter
    Chen, Pan-Pan
    Houk, Kendall N.
    Glorius, Frank
    NATURE SYNTHESIS, 2022, 1 (01): : 59 - 68
  • [34] Pd(II)-Catalyzed Direct γ-C(sp3)-H Arylation between Free β2-Amino Esters and β3-Amino Esters and Aryl Iodides Using a Catalytic Transient Directing Group
    Wang, Zhaohui
    Fu, Yangjie
    Zhang, Qiyu
    Liu, Hong
    Wang, Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12) : 7683 - 7693
  • [35] 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
  • [36] Transition-Metal-Catalyzed Arylation of Unactivated C(sp3)-H Bonds Assisted by Bidentate Directing Groups
    Zhang, Bo
    Guan, Hanxi
    Liu, Bin
    Shi, Bingfeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (08) : 1487 - 1498
  • [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] 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
  • [39] Synthesis of a Bicyclic Azetidine with In Vivo Antimalarial Activity Enabled by Stereospecific, Directed C(sp3)-H Arylation
    Maetani, Micah
    Zoller, Jochen
    Melillo, Bruno
    Verho, Oscar
    Kato, Nobutaka
    Pu, Jun
    Comer, Eamon
    Schreiber, Stuart L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (32) : 11300 - 11306
  • [40] Temperature-modulated selective C(sp3)-H or C(sp2)-H arylation through palladium catalysis
    Gogula, Thirupathi
    Zhang, Jinquan
    Lonka, Madhava Reddy
    Zhang, Shuaizhong
    Zou, Hongbin
    CHEMICAL SCIENCE, 2020, 11 (42) : 11461 - 11467