B(C6F5)3-catalyzed silylation versus reduction of phosphonic and phosphic esters with hydrosilanes

被引：22
作者：
Denis, JM
Forintos, H
Szelke, H
Keglevich, G
机构：
[1] Univ Rennes 1, CNRS, UMR 6510, F-35042 Rennes, France
[2] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 32期
关键词：
homogeneous catalysis; transesterification; reduction; hydrosilane; Lewis acidity; arylborane;
D O I：
10.1016/S0040-4039(02)01161-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
HSiR3/cat-B(C6F)(3) induced dealkylation or reduction of esters of phosphorus at 20degreesC. A specific conversion to P-silylesters occurred by reaction with tertiary silanes. In contrast, free phosphines were observed in the reaction with mono- or disubstituted silanes. A mechanism was proposed to rationalize these results. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5569 / 5571
页数：3
相关论文
共 50 条
[41]   New Synthetic Strategies for Structured Silicones Using B(C6F5)3 [J].
Brook, Michael A. ;
Grande, John B. ;
Ganachaud, Francois .
SILICON POLYMERS, 2011, 235 :161-183
[42]   (HMe2SiCH2)2: A Useful Reagent for B(C6F5)3-Catalyzed Reduction-Lactonization of Keto Acids: Concise Syntheses of (-)-cis-Whisky and (-)-cis-Cognac Lactones [J].
Xie, Hengmu ;
Lu, Ji ;
Gui, Yingying ;
Gao, Lu ;
Song, Zhenlei .
SYNLETT, 2017, 28 (18) :2453-2459
[43]   Mechanistic insights into the full hydrogenation of 2,6-substituted pyridine catalyzed by the Lewis acid C6F5(CH2)2B(C6F5)2 [J].
Zhao, Jiyang ;
Wang, Guoqiang ;
Li, Shuhua .
DALTON TRANSACTIONS, 2015, 44 (19) :9200-9208
[44]   Stoichiometric and Catalytic C-C and C-H Bond Formation with B(C6F5)3 via Cationic Intermediates [J].
Soltani, Yashar ;
Wilkins, Lewis C. ;
Melen, Rebecca L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) :11995-11999
[45]   Catalytic Selective Deoxygenation of Polyols Using the B(C6F5)3/Silane System [J].
Drosos, Nikolaos ;
Ozkal, Erhan ;
Morandi, Bill .
SYNLETT, 2016, 27 (12) :1760-1764
[46]   Boron Lewis Acid-Catalyzed Hydroboration of Alkenes with Pinacolborane: BAr3F Does What B(C6F5)3 Cannot Do [J].
Yin, Qin ;
Kemper, Sebastian ;
Klare, Hendrik F. T. ;
Oestreich, Martin .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (39) :13840-13844
[47]   Structures and Stability of Complexes of E(C6F5)3 (E = B, Al, Ga, In) with Acetonitrile [J].
Shcherbina, Nadezhda A. ;
Pomogaeva, Anna V. ;
Lisovenko, Anna S. ;
Kazakov, Igor V. ;
Gugin, Nikita Yu. ;
Khoroshilova, Olesya V. ;
Kondrat'ev, Yuri V. ;
Timoshkin, Alexey Y. .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2020, 646 (13) :873-881
[48]   Versatile Reaction Patterns of Phosphanylhydrosilylalkyne with B(C6F5)3: A Remarkable Group Substitution Effect [J].
Huang, Yanting ;
Jiang, Wenjun ;
Xi, Xin ;
Li, Yan ;
Wang, Xiaoping ;
Yang, Ming-Chung ;
Zhang, Zheng-Feng ;
Su, Ming-Der ;
Zhu, Hongping .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (36) :3496-3506
[49]   Metal-free diastereoselective catalytic hydrogenations of imines using B(C6F5)3 [J].
Heiden, Zachariah M. ;
Stephan, Douglas W. .
CHEMICAL COMMUNICATIONS, 2011, 47 (20) :5729-5731
[50]   Investigation towards the reductive amination of levulinic acid by B(C6F5)3/hydrosilane system [J].
Wang, Tianlong ;
Xu, Hai ;
He, Jianghua ;
Zhang, Yuetao .
TETRAHEDRON, 2020, 76 (36)
12345