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
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 21 条
[1]   Organophosphoryl adducts of tris(pentafluorophenyl)borane;: crystal and molecular structure of B(C6F5)3•Ph3PO [J].
Beckett, MA ;
Brassington, DS ;
Light, ME ;
Hursthouse, MB .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (11) :1768-1772
[2]  
BENIE A, 1999, THESIS U RENNES
[3]   B(C6F5)3-catalyzed silation of alcohols:: A mild, general method for synthesis of silyl ethers [J].
Blackwell, JM ;
Foster, KL ;
Beck, VH ;
Piers, WE .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4887-4892
[4]   P-H bond activation of primary phosphine-boranes: Access to alpha-hydroxy and alpha,alpha'-dihydroxyphosphine-borane adducts by uncatalyzed hydrophosphination of carbonyl derivatives [J].
Bourumeau, K ;
Gaumont, AC ;
Denis, JM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 529 (1-2) :205-213
[5]   Reversible adduct formation between phosphines and triarylboron compounds [J].
Bradley, DC ;
Harding, IS ;
Keefe, AD ;
Motevalli, M ;
Zheng, DH .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (20) :3931-3936
[6]   THE PREPARATION OF 1-1 PHOSPHINE - TRIARYLBORON COMPLEXES - THE X-RAY CRYSTAL-STRUCTURE OF (C6F5)3B.PH3 [J].
BRADLEY, DC ;
HURSTHOUSE, MB ;
MOTEVALLI, M ;
ZHENG, DH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (01) :7-8
[7]   SYNTHESIS OF PRIMARY ALPHA-CHLOROPHOSPHINES BY A CHEMOSELECTIVE REDUCTION OF ALPHA-CHLOROPHOSPHONATES [J].
CABIOCH, JL ;
PELLERIN, B ;
DENIS, JM .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1989, 44 (1-2) :27-32
[8]   Recent developments in the chemistry of amine- and phosphine-boranes [J].
Carboni, B ;
Monnier, L .
TETRAHEDRON, 1999, 55 (05) :1197-1248
[9]   REDUKTION ORGANISCHER VERBINDUNGEN DES FUNFWERTIGEN PHOSPHORS ZU PHOSPHINEN .3. DARSTELLUNG PRIMARER UND SEKUNDARER PHOSPHINE MIT SILANEN [J].
FRITZSCHE, H ;
HASSERODT, U ;
KORTE, F .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (05) :1681-+
[10]   ACCESS TO UNSTABILIZED SECONDARY VINYLPHOSPHINES BY CHEMOSELECTIVE REDUCTION OF VINYLPHOSPHINATES OR BY P-ALKYLATION OF THE PRIMARY VINYLPHOSPHINE [J].
GAUMONT, AC ;
MORISE, X ;
DENIS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4292-4295