Scope and selectivity of B(C6F5)3-catalyzed reactions of the disilane (Ph2SiH)2

被引：15

作者：

Lee, Peter T. K. ^{[1
]}

Rosenberg, Lisa ^{[1
]}

机构：

[1] Univ Victoria, Dept Chem, POB 3065, Victoria, BC V8W 3V6, Canada

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2016年 / 809卷

基金：

加拿大自然科学与工程研究理事会;

关键词：

Disilane; Si-H activation; Electrophilic borane; Homogeneous catalysis; Functionalized oligosilanes; BORANE-CATALYZED HYDROSILYLATION; METHYL-GROUP; SI-H; REDUCTION; MECHANISM; HYDROSILATION; POLYSILANES; IMINES; TRIS(PENTAFLUOROPHENYL)BORANE; HYDROGENATION;

D O I：

10.1016/j.jorganchem.2016.02.035

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The diverse catalytic activity of the electrophilic borane B(C6F5)(3) in reactions of silanes with organic substrates has been exploited extensively in studies that mostly focus on very particular, useful functional group transformations in organic synthesis. This study examines the potential for harnessing the collective, broad scope of these transformations in the preparation of new oligosilane derivatives. Borane-catalyzed hydrosilation, heterodehydrogenative coupling, and dealkylative coupling reactions of a wide range of substrates with the disilane (Ph2SiH)(2) were investigated. These allowed new mono-and disubstituted disilanes to be prepared that contain Si-O, Si-S, and Si-C linkages. Challenges and opportunities are described that arise from competing "over-reduction" chemistry, and the sensitivity of the catalysis to both the Lewis basicity and steric bulk of the substrates is examined. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：86 / 93

页数：8

共 39 条

[31] Tris(pentafluorophenyl)boron-catalyzed hydrosilation of aromatic aldehydes, ketones, and esters [J].

Parks, DJ ;

Piers, WE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (39) :9440-9441

[32] Mechanistic Aspects of Bond Activation with Perfluoroarylboranes [J].

Piers, Warren E. ;

Marwitz, Adam J. V. ;

Mercier, Lauren G. .

INORGANIC CHEMISTRY, 2011, 50 (24) :12252-12262

[33] Catalytic dehydrogenative coupling of secondary silanes using Wilkinson's catalyst [J].

Rosenberg, L ;

Davis, CW ;

Yao, JZ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (21) :5120-5121

[34] Highly efficient B(C6F5)3-catalyzed hydrosilylation of olefins [J].

Rubin, M ;

Schwier, T ;

Gevorgyan, V .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1936-1940

[35] Quantum Chemical Study of B(C6F5)3-Catalyzed Hydrosilylation of Carbonyl Group [J].

Sakata, Ken ;

Fujimoto, Hiroshi .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24) :12505-12512

[36]

Shinke S., 2005, SILICON CHEM, V3, P243, DOI DOI 10.1007/s11201-007-9026-y

[37] 3-Silylated Cyclohexa-1,4-dienes as Precursors for Gaseous Hydrosilanes: The B(C6F5)3-Catalyzed Transfer Hydrosilylation of Alkenes [J].

Simonneau, Antoine ;

Oestreich, Martin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) :11905-11907

[38] Frustrated Lewis pair catalyzed hydrosilylation and hydrosilane mediated hydrogenation of fulvenes [J].

Tamke, Sergej ;

Daniliuc, Constantin-G. ;

Paradies, Jan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (45) :9139-9144

[39] Tris(pentafluorophenyl)borane as a superior catalyst in the synthesis of optically active SiO-containing polymers [J].

Zhou, DQ ;

Kawakami, Y .

MACROMOLECULES, 2005, 38 (16) :6902-6908

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