Metal-free reduction of tertiary phosphine oxides with Hantzsch ester

被引:12
|
作者
Zhang, Tong-Xin [1 ]
Zhang, Wei-Xi [1 ]
Luo, Mei-Ming [1 ]
机构
[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China
关键词
Metal-free reduction; Tertiary phosphine oxides; Tertiary phosphines; Hantzsch ester; BOND-DISSOCIATION ENERGIES; SECONDARY;
D O I
10.1016/j.cclet.2013.09.007
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The (COCl)2/Hantzsch ester is found to be an effective system for the metal-free reduction of tertiary phosphine oxides. The reaction proceeds under mild conditions, and is applicable to triarylphosphine oxides and alkyldiarylphosphine oxides to produce the corresponding tertiary phosphines in good to excellent yields. This new finding provides a practical, convenient and metal-free method for the reduction of tertiary phosphine oxides to tertiary phosphines, and shows potential application in organic synthesis. (C) 2013 Mei-Ming Luo. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:176 / 178
页数:3
相关论文
共 50 条
  • [1] Metal-free reduction of tertiary phosphine oxides with Hantzsch ester
    Tong-Xin Zhang
    Wei-Xi Zhang
    Mei-Ming Luo
    [J]. Chinese Chemical Letters, 2014, 25 (01) : 176 - 178
  • [2] Metal-Free Reduction of Phosphine Oxides Using Polymethylhydrosiloxane
    Nicolas, Emmanuel
    Guerriero, Antonella
    Lyaskovskyy, Volodymyr
    Peruzzini, Maurizio
    Lammertsma, Koop
    Gonsalvi, Luca
    Slootweg, J. Chris
    [J]. INORGANICS, 2016, 4 (04):
  • [3] Highly Chemoselective Metal-Free Reduction of Phosphine Oxides to Phosphines
    Li, Yuehui
    Lu, Liang-Qiu
    Das, Shoubhik
    Pisiewicz, Sabine
    Junge, Kathrin
    Beller, Matthias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (44) : 18325 - 18329
  • [4] Hantzsch ester triggered metal-free cascade approach to isoindolinones
    Tian, Youping
    Wei, Junmei
    Wang, Meng
    Li, Gaoqiang
    Xu, Feng
    [J]. TETRAHEDRON LETTERS, 2018, 59 (19) : 1866 - 1870
  • [5] Rapid Metal-Free Formation of Free Phosphines from Phosphine Oxides
    Provis-Evans, Cei B.
    Emanuelsson, Emma A. C.
    Webster, Ruth L.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) : 3999 - 4004
  • [6] Metal-Free Reduction of Phosphine Oxides, Sulfoxides, and N-Oxides with Hydrosilanes using a Borinic Acid Precatalyst
    Chardon, Aurelien
    Maubert, Orianne
    Rouden, Jacques
    Blanchet, Jerome
    [J]. CHEMCATCHEM, 2017, 9 (24) : 4460 - 4464
  • [7] The Photoinduced Metal-Free Hydrotrifluoromethylation of Vinyl Phosphonates or Phosphine Oxides
    Yao, Qiuli
    Ren, Linjing
    Xiang, Dan
    Li, Kexin
    Yan, Boyu
    Ran, Maogang
    He, Jiaxin
    Zhao, Liang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (45) : 7475 - 7482
  • [8] The Reduction of Tertiary Phosphine Oxides by Silanes
    Kovacs, Tamara
    Keglevich, Gyorgy
    [J]. CURRENT ORGANIC CHEMISTRY, 2017, 21 (07) : 569 - 585
  • [9] Organocatalyzed Reduction of Tertiary Phosphine Oxides
    Schirmer, Marie-Luis
    Jopp, Stefan
    Holz, Jens
    Spannenberg, Anke
    Werner, Thomas
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) : 26 - 29
  • [10] Highly chemoselective metal-free reduction of tertiary amides
    Barbe, Guillaume
    Charette, Andr B.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) : 18 - +