Acyl anion free N-heterocyclic carbene organocatalysis

被引:707
|
作者
Ryan, Sarah J. [1 ]
Candish, Lisa [1 ]
Lupton, David W. [1 ]
机构
[1] Monash Univ, Clayton, Vic 3800, Australia
关键词
HIGHLY ENANTIOSELECTIVE SYNTHESIS; CATALYTIC-ACTIVITY; 4+2 CYCLOADDITION; 1ST EXAMPLE; KETENES; UMPOLUNG; ESTERS; MECHANISM; ALCOHOLS; ENONES;
D O I
10.1039/c3cs35522e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction discovery using N-heterocyclic carbene organocatalysis has been dominated by the chemistry of acyl anion equivalents. Recent studies demonstrate that NHCs are far more diverse catalysts, with a variety of reactions discovered that proceed without acyl anion equivalent formation. In this tutorial review selected examples of acyl anion free NHC catalysis using carbonyl compounds are presented.
引用
收藏
页码:4906 / 4917
页数:12
相关论文
共 50 条
  • [21] Single-Electron Transfer Reactions Enabled by N-Heterocyclic Carbene Organocatalysis
    Li, Qing-Zhu
    Zeng, Rong
    Han, Bo
    Li, Jun-Long
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (10) : 3238 - 3250
  • [22] Asymmetric construction of axial and planar chirality with N-heterocyclic carbene(NHC) organocatalysis
    Meng Zhang
    Xiaoqun Yang
    Xiaolin Peng
    Xiangyang Li
    Zhichao Jin
    Science China(Chemistry), 2025, 68 (03) : 815 - 825
  • [23] β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis
    Zhenqian Fu
    Jianfeng Xu
    Tingshun Zhu
    Wendy Wen Yi Leong
    Yonggui Robin Chi
    Nature Chemistry, 2013, 5 : 835 - 839
  • [24] Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now
    Pareek, Monika
    Reddi, Yernaidu
    Sunoj, Raghavan B.
    CHEMICAL SCIENCE, 2021, 12 (23) : 7973 - 7992
  • [25] β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis
    Fu, Zhenqian
    Xu, Jianfeng
    Zhu, Tingshun
    Leong, Wendy Wen Yi
    Chi, Yonggui Robin
    NATURE CHEMISTRY, 2013, 5 (10) : 835 - 839
  • [26] Generation and Reactions of an Unsubstituted N-Heterocyclic Carbene Boryl Anion
    Monot, Julien
    Solovyev, Andrey
    Bonin-Dubarle, Helene
    Derat, Etienne
    Curran, Dennis P.
    Robert, Marc
    Fensterbank, Louis
    Malacria, Max
    Lacote, Emmanuel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9166 - 9169
  • [27] Birth of organocatalysis by N-heterocyclic carbenes
    Chakraborty, Sukriyo
    Biju, Akkattu T.
    NATURE CATALYSIS, 2024, 7 (10): : 1060 - 1062
  • [28] Acyl Donor Intermediates in N-Heterocyclic Carbene Catalysis: Acyl Azolium or Azolium Enolate?
    Biswas, Animesh
    Neudoerfl, Jorg-M
    Schlorer, Nils E.
    Berkessel, Albrecht
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (09) : 4507 - 4511
  • [29] Direct Acylation of Unactivated Alkyl Halides with Aldehydes through N-Heterocyclic Carbene Organocatalysis
    Li, Qing-Zhu
    Zeng, Rong
    Xu, Peng-Shuai
    Jin, Xin-Hang
    Xie, Chuan
    Yang, Qi-Chun
    Zhang, Xiang
    Li, Jun-Long
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (40)
  • [30] Direct Acylation of Unactivated Alkyl Halides with Aldehydes through N-Heterocyclic Carbene Organocatalysis
    Li, Qing-Zhu
    Zeng, Rong
    Xu, Peng-Shuai
    Jin, Xin-Hang
    Xie, Chuan
    Yang, Qi-Chun
    Zhang, Xiang
    Li, Jun-Long
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023,