Highly efficient and selective olefination of acyl phosphonates with ethyl diazoacetate catalyzed by a cobalt(II) porphyrin complex

被引:14
|
作者
Erturk, Erkan [1 ]
Demir, Ayhan S. [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
关键词
D O I
10.1016/j.tet.2008.05.108
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cobalt(II) porphyrin complex (CoTPP) was found to be an efficient catalyst for the Wittig type olefination of acyl phosphonates with ethyl diazoacetate (EDA) in the presence of triphenylphosphine (Ph3P). By using this one pot methodology under mild conditions, densely functionalized vinyl phosphonates were obtained in high yields and high E/Z selectivities in relatively short reaction times. A rather broad substrate spectrum and steric influence on the reaction rate were observed. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7555 / 7560
页数:6
相关论文
共 50 条
  • [41] HIGHLY SELECTIVE ALDOL REACTION OF DIBENZOYLMETHANES WITH FORMALDEHYDE CATALYZED BY COBALT SCHIFF-BASE COMPLEX UNDER NEUTRAL CONDITIONS
    MARUYAMA, K
    KUBO, K
    TODA, Y
    KAWASE, K
    MASHINO, T
    NISHINAGA, A
    TETRAHEDRON LETTERS, 1995, 36 (31) : 5609 - 5612
  • [42] Cu(II)-catalyzed highly regio- and stereoselective construction of C-C double bonds: an efficient method for the ketonization-olefination of indoles
    Bao, Yun-Hong
    Zhu, Jia-Yi
    Qin, Wen-Bing
    Kong, Yu-Bo
    Chen, Zheng-Wang
    Tang, Shao-Bin
    Liu, Liang-Xian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (45) : 7938 - 7945
  • [43] Dirhodium(II)-Catalyzed Annulation of Enoldiazoacetamides with α-Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems
    Cheng, Qing-Qing
    Yedoyan, Julietta
    Arman, Hadi
    Doyle, Michael P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) : 5573 - 5576
  • [44] Highly efficient and selective epoxidation of alkenes by photochemical oxygenation sensitized by a ruthenium(II) porphyrin with water as both electron and oxygen donor
    Funyu, S
    Isobe, T
    Takagi, S
    Tryk, DA
    Inoue, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) : 5734 - 5740
  • [45] Cobalt(II)-complex modified Ag electrode for efficient and selective electrochemical reduction of CO2 to CO
    Jiang, Xingxin
    Ren, Xiaohui
    Chen, Rongsheng
    Ma, Feng
    He, Wenping
    Zhang, Tian
    Wen, Ying
    Shi, Li
    Ren, Long
    Liu, Huating
    Wang, Xusheng
    Ni, Hongwei
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2023, 949
  • [47] Completely Eradicating Singlet Oxygen in Li-O2 Battery via Cobalt(II)-Porphyrin Complex-Catalyzed LiOH Chemistry
    Feng, Hui
    Yang, Qi
    Li, Chao
    Lin, Yang
    Liu, Haigang
    Zhang, Nian
    Hu, Bingwen
    JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2023, 14 (04): : 846 - 853
  • [48] Bis-dimethylaminobenzaldehyde Schiff-Base Cobalt(II) Complex as a Neutral Carrier for a Highly Selective Iodide Electrode
    Jianyuan Dai
    Yaqin Chai
    Ruo Yuan
    Xia Zhong
    Yan Liu
    Dianping Tang
    Analytical Sciences, 2004, 20 : 1661 - 1665
  • [49] Bis-dimethylaminobenzaldehyde schiff-base cobalt(II) complex as a neutral carrier for a highly selective iodide electrode
    Dai, JY
    Chai, YQ
    Yuan, R
    Zhong, X
    Liu, Y
    Tang, DP
    ANALYTICAL SCIENCES, 2004, 20 (12) : 1661 - 1665
  • [50] Highly Selective, Efficient Deoxygenative Hydrogenation of Amides Catalyzed by a Manganese Pincer Complex via Metal-Ligand Cooperation
    Zou, You-Quan
    Chakraborty, Subrata
    Nerush, Alexander
    Oren, Dror
    Diskin-Posner, Yael
    Ben-David, Yehoshoa
    Milstein, David
    ACS CATALYSIS, 2018, 8 (09): : 8014 - 8019