N-Heterocyclic Carbene Catalyzed Sulfenylation of α,β-Unsaturated Aldehydes

被引:38
|
作者
Dong, Yu-Ting [1 ]
Jim, Quan [1 ]
Zhou, Ling [1 ]
Chen, Jie [1 ]
机构
[1] Northwest Univ, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Dept Chem & Mat Sci, Xian 710127, Peoples R China
基金
中国国家自然科学基金;
关键词
BAYLIS-HILLMAN REACTION; SULFUR BOND FORMATION; CARBON-SULFUR; BRESLOW INTERMEDIATE; NHC CATALYSIS; UMPOLUNG; ACTIVATION; ACYL; THIOESTERIFICATION; ORGANOCATALYSIS;
D O I
10.1021/acs.orglett.6b02939
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient N-heterocyclic carbene (NHC) catalyzed sulfenylation reaction of alpha,beta-unsaturated aldehydes with N-(arylthio)phthalimide has been developed. A wide variety of alpha-thioenals can be obtained with good to excellent yields and excellent Z-configuration.
引用
收藏
页码:5708 / 5711
页数:4
相关论文
共 50 条
  • [21] N-Heterocyclic Carbene-Catalyzed Cyclization of Unsaturated Acyl Chlorides and Ketones
    Shen, Li-Tao
    Shao, Pan-Lin
    Ye, Song
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) : 1943 - 1948
  • [22] α′-Hydroxyenones as Mechanistic Probes and Scope-Expanding Surrogates for α,β-Unsaturated Aldehydes in N-Heterocyclic Carbene-Catalyzed Reactions
    Chiang, Pei-Chen
    Rommel, Michael
    Bode, Jeffrey W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) : 8714 - 8718
  • [23] N-Heterocyclic Carbene Catalyzed Reactions of α-Bromo-α,β-unsaturated Aldehydes/α,β-Dibromoaldehydes with 1,3-Dinucleophilic Reagents
    Yao, Changsheng
    Wang, Donglin
    Lu, Jun
    Li, Tuanjie
    Jiao, Weihui
    Yu, Chenxia
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (07) : 1914 - 1917
  • [24] N-heterocyclic carbene-catalysed pentafluorophenylation of aldehydes
    Du, Guang-Fen
    Xing, Fen
    Gu, Cheng-Zhi
    Dai, Bin
    He, Lin
    [J]. RSC ADVANCES, 2015, 5 (45): : 35513 - 35517
  • [25] N-Heterocyclic Carbene Catalyzed Radical Coupling of Aldehydes with Redox-Active Esters
    Song, Runjiang
    Chi, Yonggui Robin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) : 8628 - 8630
  • [26] Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Allylation of Aldehydes with Allylic Carbonates
    Takemoto, Shunsuke
    Ishii, Takuya
    Yasuda, Shigeo
    Ohmiya, Hirohisa
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2019, 92 (05) : 937 - 940
  • [27] N-Heterocyclic Carbene-Catalyzed Monoacylation of 1,4-Naphthoquinones with Aldehydes
    Teresa Molina, Maria
    Navarro, Cristina
    Moreno, Ana
    Csaky, Aurelio G.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24): : 9573 - 9575
  • [28] N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Aldehydes with Arylsulfonyl Indoles
    Li, Yi
    Shi, Fu-Qiang
    He, Qing-Li
    You, Shu-Li
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3182 - 3185
  • [29] Highly efficient trialkylsilylcyanation of aldehydes, ketones and imines catalyzed by a nucleophilic N-heterocyclic carbene
    Kano, Taichi
    Sasaki, Kouji
    Konishi, Teppei
    Mii, Haruka
    Maruoka, Keiji
    [J]. TETRAHEDRON LETTERS, 2006, 47 (27) : 4615 - 4618
  • [30] N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes
    Zhao, Wei
    Liu, Jing
    He, Xiangkui
    Jiang, Hao
    Lu, Liangqiu
    Xiao, Wenjing
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (08) : 2504 - 2514