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Organosilicon Chemistry

Organosilicon Chemistry

Publisher VCH
Year 01/12/2019
Edition First
Pages 568
Version hardback
Readership level Professional and scholarly
Language English
ISBN 9783527344536
Categories Chemistry
$226.64 (with VAT)
854.72 PLN / €192.01 / £174.88
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Book description

Provides a unique summary of important catalytic reactions in the presence of silicon A must-have for all synthetic chemists, this book summarizes all of the important developments in the application of organosilicon compounds in organic synthesis and catalysis. Edited by two world leaders in the field, it describes different approaches and covers a broad range of reactions, e.g. catalytic generation of silicon nucleophiles, Si-H Bond activation, C-H bond silylation, silicon-based cross-coupling reactions, and hydrosilylation in the presence of earth-abundant metals. In addition to the topics covered above, Organosilicon Chemistry: Novel Approaches and Reactions features chapters that look at Lewis base activation of silicon Lewis acids, silylenes as ligands in catalysis, and chiral silicon molecules. -The first book about this topic in decades, covering a broad range of reactions -Covers new approaches and novel catalyst systems that have been developed in recent years -Written by well-known, international experts in the areas of organometallic silicon chemistry and organosilicon cross-coupling reactions Organosilicon Chemistry: Novel Approaches and Reactions is an indispensable source of information for synthetic chemists in academia and industry, working in the field of organic synthesis, catalysis, and main-group chemistry.

Organosilicon Chemistry

Table of contents

Foreword xiii

Preface xv

1 Catalytic Generation of Silicon Nucleophiles 1
Koji Kubota and Hajime Ito

1.1 Introduction 1

1.2 Silicon Nucleophiles with Copper Catalysts 2

1.2.1 Copper-Catalyzed Nucleophilic Silylation with Disilanes 2 Silylation of , -Unsaturated Carbonyl Compounds 2 Silylation of Alkylidene Malonates 3 Silylation of Allylic Carbamates 3

1.2.2 Copper-Catalyzed Nucleophilic Silylation with Silylboronate 4 Silicon-Boron Bond Activation with Copper Alkoxide 4 Silylation of , -Unsaturated Carbonyl Compounds 4 Catalytic Allylic Silylation 7 Catalytic Silylation of Imines 9 Catalytic Silylation of Aldehydes 9 Catalytic Synthesis of Acylsilanes 11 Silylative Carboxylation with CO2 11 CO2 Reduction via Silylation 13 Silyl Substitution of Alkyl Electrophiles 13 Decarboxylative Silylation 14 Silylative Cyclization 15 Silylative Allylation of Ketones 15 Silylation of Alkynes 16 Propargylic Substitution 19

1.2.3 Copper-Catalyzed Nucleophilic Silylation with Silylzincs 20

1.3 Silicon Nucleophiles with Rhodium Catalysts 21

1.3.1 Rhodium-Catalyzed Nucleophilic Silylation with Disilanes 21

1.3.2 Rhodium-Catalyzed Nucleophilic Silylation with Silylboronates 21 Conjugate Silylation 21 Coupling between Propargylic Carbonates to Form Allenylsilanes 22

1.4 Silicon Nucleophiles with Nickel Catalysts 22

1.4.1 Nickel-Catalyzed Nucleophilic Silylation with Alkyl Electrophiles 22

1.5 Silicon Nucleophiles with Lewis Base Catalysts 23

1.5.1 N-Heterocyclic Carbene-Catalyzed Nucleophilic 1,4-Silylation 23

1.5.2 Alkoxide Base-Catalyzed 1,2-Silaboration 24

1.5.3 Phosphine-Catalyzed 1,2-Silaboration 24

1.6 Closing Remarks 25

Abbreviations 25

References 26

2 Si?H Bond Activation by Main-Group Lewis Acids 33
Dieter Weber and Michel R. Gagne

2.1 Introduction to Silanes and the Si?H bond 33

2.1.1 Overview of the Discovery and the History of Silanes 33

2.1.2 A Comparison of Hydrocarbons and Hydrosilicons 34

2.1.3 Stability of the Silicon-Hydrogen Bond 35

2.1.4 The Silylium Ion 35

2.2 The Activation of Si?H Bonds by Boron Lewis Acids 36

2.2.1 Tris(pentafluorophenyl)borane (BCF) 36

2.2.2 The Catalytic Activation of Si?H Bonds by BCF and Other Boranes 36 The Mechanism of Borane-Catalyzed Si?H Bond Activation 36 Additional Mechanistic Aspects 38

2.2.3 Categorizing Reduct

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