Highly chemoselective intermolecular cross-benzoin reactions using an ad hoc designed novel N-heterocyclic carbene catalyst

被引:17
|
作者
Delany, Eoghan G. [1 ]
Connon, Stephen J. [1 ]
机构
[1] Trinity Coll Dublin, Sch Chem, Trinity Biomed Sci Inst, 152-160 Pearse St, Dublin 2, Ireland
关键词
TRIAZOLIUM SALTS; ACYLOIN CONDENSATIONS; BRESLOW INTERMEDIATE; ASYMMETRIC-SYNTHESIS; ALIPHATIC-ALDEHYDES; UMPOLUNG; ORGANOCATALYSIS; GENERATION;
D O I
10.1039/c7ob03005c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design of a novel N-heterocyclic carbene catalyst incorporating a bulky yet highly electron-deficient N-aryl substituent has allowed the development of an efficient protocol for the first highly chemoselective intermolecular benzoin condensations between two non-identical aromatic aldehydes.
引用
收藏
页码:780 / 786
页数:7
相关论文
共 50 条
  • [21] N-Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions
    Biju, Akkattu T.
    Padmanaban, Mohan
    Wurz, Nathalie E.
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) : 8412 - 8415
  • [22] Enantioselective N-heterocyclic carbene-catalysed intermolecular crossed benzoin condensations: Improved catalyst design and the role of in situ racemisation
    Delany, Eoghan G.
    Connon, Stephen J.
    Organic and Biomolecular Chemistry, 2021, 19 (01): : 248 - 258
  • [23] Enantioselective N-heterocyclic carbene-catalysed intermolecular crossed benzoin condensations: improved catalyst design and the role of in situ racemisation
    Delany, Eoghan G.
    Connon, Stephen J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (01) : 248 - 258
  • [24] N-Heterocyclic Carbene Catalyzed Highly Chemoselective Intermolecular Crossed Acyloin Condensation of Aromatic Aldehydes with Trifluoroacetaldehyde Ethyl Hemiacetal
    Ramanjaneyulu, Bandaru T.
    Mahesh, Sriram
    Anand, Ramasamy Vijaya
    ORGANIC LETTERS, 2015, 17 (01) : 6 - 9
  • [25] Copper N-Heterocyclic Carbene: A Catalyst for Aerobic Oxidation or Reduction Reactions
    Zhan, Le-Wu
    Han, Lei
    Xing, Ping
    Jiang, Biao
    ORGANIC LETTERS, 2015, 17 (24) : 5990 - 5993
  • [26] Recent Progress of Supported N-Heterocyclic Carbene Catalyst in Organic Reactions
    Li, Xiaowei
    Zhou, Jin
    Zhuo, Shuping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (07) : 1484 - 1500
  • [27] Inverse Enantioselectivity with Catalyst Loading in Enantioselective Self-Benzoin Condensation using Triazolium-based N-Heterocyclic Carbene Catalyst
    Mao, Hui
    An, Shu Lan
    Kim, Sun Min
    Yang, Jung Woon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (12): : 4408 - 4410
  • [28] Synthesis and characterization of a novel recyclable palladium N-heterocyclic carbene catalyst
    Pelter, Libbie S. W.
    Kmiotek, Kraig R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [29] A Family of Thiazolium Salt Derived N-Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross-Benzoin Condensation
    Piel, Isabel
    Pawelczyk, Marius D.
    Hirano, Keiichi
    Froehlich, Roland
    Glorius, Frank
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) : 5475 - 5484
  • [30] Asymmetric synthesis of chromanones via N-heterocyclic carbene catalyzed intramolecular crossed-benzoin reactions
    Enders, Dieter
    Niemeier, Oliver
    Raabe, Gerhard
    SYNLETT, 2006, (15) : 2431 - 2434