Gold Catalysis: An Homogeneous Approach

564 Pages·2014·3.754 MB·English

by  F Dean Toste, Veronique Michelet (eds.)

Gold Catalysis
An Homogeneous Approach
P831_9781848168527_tp.indd 1 15/5/14 7:55 pm
CATALYTIC SCIENCE SERIES
Series Editor: Graham J. Hutchings (Cardiff University)
Published
Vol. 1 Environmental Catalysis
edited by F. J. J. G. Janssen and R. A. van Santen
Vol. 2 Catalysis by Ceria and Related Materials
edited by A. Trovarelli
Vol. 3 Zeolites for Cleaner Technologies
edited by M. Guisnet and J.-P. Gilson
Vol. 4 Isotopes in Heterogeneous Catalysis
edited by Justin S. J. Hargreaves, S. D. Jackson and G. Webb
Vol. 5 Supported Metals in Catalysis
edited by J. A. Anderson and M. F. García
Vol. 6 Catalysis by Gold
edited by G. C. Bond, C. Louis and D. T. Thompson
Vol. 7 Combinatorial Development of Solid Catalytic Materials:
Design of High-Throughput Experiments, Data Analysis, Data Mining
edited by M. Baerns and M. Hole ňa
Vol. 8 Petrochemical Economics: Technology Selection in a Carbon Constrained World
by D. Seddon
Vol. 9 Deactivation and Regeneration of Zeolite Catalysts
edited by M. Guisnet and F. R. Ribeiro
Vol. 10 Concepts in Syngas Manufacture
by J. Rostrup-Nielsen and L. J. Christiansen
Vol. 11 Supported Metals in Catalysis (2nd Edition)
by J. A. Anderson
Vol. 12 Catalysis by Ceria and Related Materials (2nd Edition)
edited by A. Trovarelli and P. Fornasiero
Vol. 13 Gold Catalysis: An Homogeneous Approach
edited by F. Dean Toste and Véronique Michelet
CATALYTIC SCIENCE SERIES — VOL. 13
Series Editor: Graham J. Hutchings
Gold Catalysis
An Homogeneous Approach
edited by
F. Dean Toste
University of California Berkeley, USA
Véronique Michelet
Chimie ParisTech, France
Imperial College Press
ICP
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Published by
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Catalytic Science Series — Vol. 13
GOLD CATALYSIS
An Homogeneous Approach
Copyright © 2014 by Imperial College Press
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b1759 Gold Catalysis: An Homogenous Approach
CONTENTS
Contributors xiii
Chapter 1 From Gold in Nature to Gold Catalysts ........................1
Søren Kramer and Fabien Gagosz
1.1 The Gold Element: An Overview .................................................1
1.1.1 History of gold ....................................................................1
1.1.2 Abundance, production, and stocks ..................................2
1.1.3 Demand and supply ............................................................3
1.1.4 Price .....................................................................................3
1.1.5 General physical and chemical properties ........................4
1.1.6 Applications .........................................................................4
1.2 History of Homogeneous Gold Catalysis.....................................5
1.3 General Reactivity of Electrophilic Gold Species .......................9
1.4 Gold Catalysts ..............................................................................14
1.4.1 Inorganic gold catalysts ....................................................16
1.4.2 Gold complexes ................................................................19
1.4.3 Chiral catalysts ...................................................................34
1.5 Conclusion...................................................................................38
References ..........................................................................................40
Chapter 2 Homogeneous Gold-Catalyzed Oxidation
and Reduction Reactions ..............................................51
Liming Zhang
2.1 Introduction ................................................................................51
2.2 Homogeneous Gold-Catalyzed Oxidation Reactions
with External Oxidants ...............................................................52
v
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2.2.1 Alkyne or allene as substrate ............................................52
2.2.2 Alkenes as substrates .........................................................67
2.2.3 Alcohol and sulfides as substrates ....................................71
2.3 Homogeneous Gold-Catalyzed Intramolecular
Redox Reactions .........................................................................71
2.3.1 With tether oxidants .........................................................71
2.3.2 Involving hydride migration ...........................................77
2.4 Homogeneous Gold-Catalyzed Reductions ...............................79
2.5 Summary ......................................................................................80
2.6 Acknowledgment ........................................................................80
References ..........................................................................................81
Chapter 3 Gold-Catalyzed Addition of Carbon
Nucleophiles to C–C Multiple Bonds,
Carbonyls, and other Electrophiles .............................87
Bryon L. Simmons and Hong C. Shen
3.1 Introduction ................................................................................87
3.2 Addition of Carbon Nucleophiles to Alkynes ...........................88
3.2.1 Addition of enols, silyl enol ethers, and silyl ketene
amides to alkynes ..............................................................88
3.2.2 Addition of enamine derivatives to alkynes ....................92
3.2.3 Addition of arenes to alkynes...........................................93
3.2.4 Addition of alkenes to alkynes .........................................99
3.2.5 Addition of allyls to C–C multiple bonds ......................104
3.2.6 Addition of allenes to alkynes ........................................107
3.2.7 Addition of carbenes to alkynes .....................................108
3.3 Addition of Carbon Nucleophiles to Allenes ..........................108
3.4 Addition of Carbon Nucleophiles to Alkenes .........................114
3.5 Addition of Carbon Nucleophiles to Carbonyls .....................119
3.6 Addition of Carbon Nucleophiles to Iminiums ......................122
3.7 Addition of Arenes and Alkenes to Miscellaneous
Electrophiles..............................................................................122
3.8 Conclusion.................................................................................129
References ........................................................................................130
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Contents vii
Chapter 4 Gold-Catalyzed Addition of Heteroatom
Nucleophile to C–C Multiple Bond ...........................137
Naoki Asao, Naoya Hatakeyama and
Yoshinori Yamamoto
4.1 Introduction ..............................................................................137
4.2 Nitrogen Nucleophiles ............................................................137
4.2.1 Addition to alkynes .........................................................137
4.2.2 Addition to allenes ..........................................................141
4.2.3 Addition to alkenes and dienes .....................................143
4.3 Oxygen Nucleophiles ...............................................................145
4.3.1 Addition to alkynes .........................................................145
4.3.2 Addition to allenes ..........................................................161
4.3.3 Addition to alkenes and dienes .....................................162
4.4 Sulfur Nucleophiles ..................................................................164
4.5 Other Heteroatom Nucleophiles ............................................165
4.6 Conclusion.................................................................................166
References ........................................................................................166
Chapter 5 Gold-Catalyzed Synthesis of Heterocycles ...............175
Antonio Arcadi
5.1 Introduction ..............................................................................175
5.2 Synthesis of Heterocycles via Gold-Catalyzed Heteroatom
Addition to Unsaturated C–C Bonds.......................................176
5.2.1 Synthesis of heterocyclic compounds through
intermolecular hydrofunctionalization of alkynes .......177
5.2.2 Synthesis of heterocyclic compounds through
intramolecular hydrofunctionalization of alkynes,
allenes, and alkenes ........................................................180
5.2.3 Heterocyclization of alkynes tethered with
carbonyl groups...............................................................188
5.2.4 Gold-catalyzed migratory cyclizations ............................191
5.3 Synthesis of Heterocyclic Derivatives through
Gold-Catalyzed Cyclization of Polyunsaturated
Compounds ...............................................................................193
α
5.4 Synthesis of Heterocyclic Compounds via -Oxo
Gold Carbenoid ........................................................................196
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viii Contents
5.5 Synthesis of Heterocyclic Derivatives through
Gold-Catalyzed Cycloaddition Reactions .................................201
5.6 Synthesis of Heterocyclic Derivatives through
Gold-Catalyzed Activation of Carbonyl Groups
and Alcohols ..............................................................................203
5.7 Synthesis of Heterocyclic Compounds through
Gold-Mediated C–H Bond Functionalization .........................206
5.7.1 Direct C–H functionalization of heterocycles ...............206
5.7.2 Intramolecular gold-catalyzed hydroarylation
reactions ..........................................................................208
5.7.3 Alkyne C–H and C –H functionalization ....................211
sp3
5.8 Gold-Catalyzed Domino Cyclization/Oxidative
Coupling Reactions ...................................................................212
5.9 Conclusions ...............................................................................215
References ........................................................................................217
Chapter 6 Gold-Catalyzed Multi-Component Reactions ............225
Rachid Skouta and Chao- Jun Li
6.1 Introduction ..............................................................................225
6.2 Gold-Catalyzed Three-Component Reactions .........................226
6.2.1 Aldehydes, terminal alkynes, and amines .....................226
6.2.2 Aldehydes, terminal alkynes, and
triethylorthoformate .......................................................234
6.2.3 Aldehydes, ketones, and carbamates .............................234
6.2.4 Imines, acyl chlorides, and terminal alkynes ................236
6.2.5 Acetylenedicarboxylates, quinoline/isoquinoline,
and terminal alkynes .......................................................237
6.2.6 (Arylmethylene)cyclopropylcarbinols, terminal
alkynes, and alcohols ......................................................239
6.2.7 Amines, internal alkynes, and terminal alkynes ...........240
6.2.8 Alkenes, boronic acid, and oxygen nucleophiles .........242
6.3 Gold-Catalyzed Three-Component Reactions/Tandem
Cyclization .................................................................................243
6.3.1 Aldehydes, terminal alkynes, and amines/
Cycloisomerization ..........................................................243
6.3.2 Glyoxylic acid, alkynes, and amines/Intramolecular
cyclization ........................................................................244
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Contents ix
6.3.3 Enantioselective [4 + 2] cycloaddition/
Intramolecular hydroamination ....................................246
6.4 Concluding Remarks ................................................................247
6.5 Acknowledgments .....................................................................247
References ........................................................................................248
Chapter 7 Gold Catalysis on Tandem and Cascade
Reactions ......................................................................253
Rai-Shung Liu
7.1 Introduction ..............................................................................253
7.2 Oxo Alkynes ..............................................................................254
7.3 Oxodienes .................................................................................263
7.4 Iminoalkynes .............................................................................266
7.5 Aminoalkynes ............................................................................266
7.6 Nitroalkyne ................................................................................266
7.7 Alkynyl Nitrone .........................................................................267
7.8 Allenyl Acetals ...........................................................................268
7.9 Epoxyalkynes .............................................................................269
7.10 Alkynyl Hydroxylamine ..........................................................270
7.11 Conclusion...............................................................................271
References ........................................................................................271
Chapter 8 Cycloisomerization Reactions of 1, N-Enynes ..........275
Núria Huguet and Antonio M. Echavarren
8.1 Introduction .............................................................................275
8.2 Gold Complexes ......................................................................275
8.3 Gold-Catalyzed Cyclization of 1, n-Enynes ..............................278
8.3.1 Gold-catalyzed cycloisomerizations of 1, 6-enynes ........278
8.3.2 Gold-catalyzed cycloisomerizations and skeletal
rearrangement of 1, 5-enynes .......................................293
8.3.3 Gold-catalyzed cycloisomerizations and skeletal
rearrangement of 1, n-enynes (n > 6) ...........................309
8.3.4 Intermolecular reactions of alkynes with alkenes
and [2 + 2] cycloadditions..............................................311
References ........................................................................................314
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