Noncovalent interactions in catalysis

675 Pages·2019·64.437 MB·English

by  Kopylovich, Maximilian N., Mahmudov, Kamran T., Pombeiro, Armando J., Silva, M. Fátima C. Guedes da

Noncovalent Interactions in Catalysis
1
0
0
P
F
0-
9
4
6
1
0
8
8
7
1
8
7
9
9/
3
0
1
0.
1
oi:
d
g |
or
c.
s
s.r
b
u
p
s://
p
htt
n
o
9
1
0
2
h
c
ar
M
4
0
n
o
d
e
h
s
bli
u
P
View Online
Catalysis Series
Editor-in-chief:
Justin S. J. Hargreaves, University of Glasgow, UK
1
0
0
P Series editors:
F
0- Bert Klein Gebbink, Utrecht University, The Netherlands
9
4
6 Jose Rodriguez, Brookhaven National Laboratory, USA
1
0
8
8
7
1 Titles in the series:
8
7
9/9 1: Carbons and Carbon Supported Catalysts in Hydroprocessing
03 2: Chiral Sulfur Ligands: Asymmetric Catalysis
1
0. 3: Recent Developments in Asymmetric Organocatalysis
1
oi: 4: Catalysis in the Refining of Fischer–Tropsch Syncrude
d
g | 5: Organocatalytic Enantioselective Conjugate Addition Reactions: A Power-
or
c. ful Tool for the Stereocontrolled Synthesis of Complex Molecules
s
s.r 6: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient
b
u
p Synthetic Tools
ps:// 7: P-Stereogenic Ligands in Enantioselective Catalysis
n htt 8: Chemistry of the Morita–Baylis–Hillman Reaction
o
9 9: Proton-coupled Electron Transfer: A Carrefour of Chemical Reactivity
1
20 Traditions
h
c 10: Asymmetric Domino Reactions
ar
M 11: C–H and C–X Bond Functionalization: Transition Metal Mediation
4
0 12: Metal Organic Frameworks as Heterogeneous Catalysts
n
d o 13: Environmental Catalysis Over Gold-based Materials
e
sh 14: Computational Catalysis
ubli 15: Catalysis in Ionic Liquids: From Catalyst Synthesis to Application
P
View Online
16: Economic Synthesis of Heterocycles: Zinc, Iron, Copper, Cobalt, Manga-
nese and Nickel Catalysts
17: Metal Nanoparticles for Catalysis: Advances and Applications
18: Heterogeneous Gold Catalysts and Catalysis
19: Conjugated Linoleic Acids and Conjugated Vegetable Oils
1
0
0 20: Enantioselective Multicatalysed Tandem Reactions
P
F
0- 21: New Trends in Cross-coupling: Theory and Applications
9
64 22: Atomically-precise Methods for Synthesis of Solid Catalysts
1
80 23: Nanostructured Carbon Materials for Catalysis
8
17 24: Heterocycles from Double-functionalized Arenes: Transition Metal
8
97 Catalyzed Coupling Reactions
9/
3 25: Asymmetric Functionalization of C–H Bonds
0
1
0. 26: Enantioselective Nickel-catalysed Transformations
1
oi: 27: N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient
d
g | Synthetic Tools, 2nd edition
or 28: Zeolites in Catalysis: Properties and Applications
c.
s.rs 29: Biocatalysis: An Industrial Perspective
b
u 30: Dienamine Catalysis for Organic Synthesis
p
s:// 31: Metal-free Functionalized Carbons in Catalysis: Synthesis, Characteriza-
p
htt tion and Applications
n
o 32: Modern Biocatalysis: Advances Towards Synthetic Biological Systems
9
201 33: NOx Trap Catalysts and Technologies: Fundamentals and Industrial
h Applications
c
Mar 34: Alternative Catalytic Materials: Carbides, Nitrides, Phosphides and
4 Amorphous Boron Alloys
0
on 35: Enantioselective Cobalt-catalysed Transformations
d
he 36: Noncovalent Interactions in Catalysis
s
bli
u
P
How to obtain future titles on publication:
A standing order plan is available for this series. A standing order will bring
delivery of each new volume immediately on publication.
For further information please contact:
Book Sales Department, Royal Society of Chemistry, Thomas Graham House,
Science Park, Milton Road, Cambridge, CB4 0WF, UK
Telephone: [phone], Fax: [phone]
Email: [email protected]
Visit our website at www.rsc.org/books
View Online
1
0
0
P
F
0-
9
4
6
1
0
8
8
7
1
8
7
9
9/
3
0
1
10.
oi:
d
g |
or
c.
s
s.r
b
u
p
s://
p
htt
n
o
9
1
0
2
h
c
ar
M
4
0
n
o
d
e
h
s
bli
u
P
View Online
Noncovalent Interactions in
Catalysis
1
0
0
P
F
0-
9
4
6
1
80 Edited by
8
7
1
8
97 Kamran T. Mahmudov
9/
03 University of Lisbon, Portugal
1
0. Email: [email protected]
1
oi:
d
g | Maximilian N. Kopylovich
or
c. University of Lisbon, Portugal
s
s.r Email: [email protected]
b
u
p
ps:// M. Fátima C. Guedes da Silva
n htt University of Lisbon, Portugal
o
9 Email: [email protected]
1
0
2
h
c Armando J. L. Pombeiro
ar
M
University of Lisbon, Portugal
4
n 0 Email: [email protected]
o
d
e
h
s
bli
u
P
View Online
1
0
0
P
F
0-
9
4
6
1
0
8
8
7
1
78 Catalysis Series No. 36
9
9/
03 Print ISBN: 978-1-78801-468-7
1
0. PDF ISBN: 978-1-78801-649-0
1
oi: EPUB ISBN: 978-1-78801-751-0
d
g | Print: ISSN: 1757-6725
or Electronic ISSN: 1757-6733
c.
s
bs.r A catalogue record for this book is available from the British Library
u
p
s:// © The Royal Society of Chemistry 2019
p
htt
n All rights reserved
o
9
1
20 Apart from fair dealing for the purposes of research for non-commercial purposes or for
ch private study, criticism or review, as permitted under the Copyright, Designs and Patents
ar
M Act 1988 and the Copyright and Related Rights Regulations 2003, this publication may
04 not be reproduced, stored or transmitted, in any form or by any means, without the prior
on permission in writing of The Royal Society of Chemistry or the copyright owner, or in
d
e the case of reproduction in accordance with the terms of licences issued by the Copyright
h
blis Licensing Agency in the UK, or in accordance with the terms of the licences issued by the
Pu appropriate Reproduction Rights Organization outside the UK. Enquiries concerning
reproduction outside the terms stated here should be sent to The Royal Society of
Chemistry at the address printed on this page.
Whilst this material has been produced with all due care, The Royal Society of Chemistry
cannot be held responsible or liable for its accuracy and completeness, nor for any
consequences arising from any errors or the use of the information contained in this
publication. The publication of advertisements does not constitute any endorsement by
The Royal Society of Chemistry or Authors of any products advertised. The views and
opinions advanced by contributors do not necessarily reflect those of The Royal Society
of Chemistry which shall not be liable for any resulting loss or damage arising as a result
of reliance upon this material.
The Royal Society of Chemistry is a charity, registered in England and Wales, Number
207890, and a company incorporated in England by Royal Charter (Registered No.
RC000524), registered office: Burlington House, Piccadilly, London W1J 0BA, UK,
Telephone: [phone].
For further information see our web site at www.rsc.org
Printed in the United Kingdom by CPI Group (UK) Ltd, Croydon, CR0 4YY, UK
7
0
0
P
F
90- Preface
4
6
1
0
8
8
7
1
8
7
9
9/
3
0
1
0. Inter- and intramolecular noncovalent interactions play a fundamental role
1
oi: in synthesis, catalysis, crystal engineering, electrochemistry, molecular rec-
d
g | ognition, biology, material sciences, etc. In fact, enzymatic and synthetic
c.or catalytic processes can involve noncovalent interaction-supported transi-
s
s.r tion states and intermediates, which concern crucial stage(s) concerning the
b
pu selectivity and the outcome of the reactions. This book aims to discuss and
s:// demonstrate the key roles of noncovalent interactions in transition states
p
htt and intermediates. In particular, many metal complex-catalysed reactions
n
9 o and organocatalytic transformations are known to occur via noncovalent
1
0 interactions between the starting material(s) and the catalyst. An in-depth
2
ch understanding of these weak forces can lead to the design of efficient syn-
ar
M thetic catalysts and to better control the reactivity.
4
0 The hydrogen bond, agostic, anagostic, cation–π, anion–π and π–π inter-
n
d o actions are the most versatile and explored/understood noncovalent interac-
e
h tions in catalysis. However, the use in catalysis of the “young” noncovalent
s
bli interactions, such as halogen, chalcogen, pnictogen, tetrel and icosagen
u
P
bonds, is still in its early stages. In comparison with other types of noncova-
lent interactions, these “young” weak forces are more directional and more
hydrophobic, characteristics that make them a unique tool in catalysis for
selective transformations.
Following our previous book on the overall field of noncovalent interactions
(Non-covalent Interactions in the Synthesis and Design of New Compounds, John
Wiley &Sons, Hoboken, NJ, 2016, http://dx.doi.org/10.1002/9781119113874),
the present book addresses more specifically the field of catalysis. It com-
prises 29 chapters with contributions from active researchers in the field of
synthesis and catalysis, with various viewpoints. Comprehensive discussions

Catalysis Series No. 36
Noncovalent Interactions in Catalysis
Edited by Kamran T. Mahmudov, Maximilian N. Kopylovich, M. Fátima C. Guedes da Silva and 
Armando J. L. Pombeiro
© The Royal Society of Chemistry 2019
Published by the Royal Society of Chemistry, www.rsc.org
vii
View Online
viii Preface
on the roles of different types of noncovalent interactions in transition states
and intermediates in homogeneous and heterogeneous catalysis are pre-
sented. However, owing to the collective actions of noncovalent interactions
in catalysis, we organized the sections according to the types of these weak
forces.
7
0
0 Chapter 1 highlights the role of different types of noncovalent interactions
P
F
0- in C–H bond functionalization in various classes of organic compounds.
9
64 Chapter 2 focuses on the importance of C–H hydrogen bonding in asymmet-
1
80 ric catalysis. Cooperative actions of multiple hydrogen bonds in catalysis are
8
17 described in Chapter 3. Secondary (agostic Si–H/electrostatic C–F) interac-
8
97 tions in alkaline earth-based catalysts are reported in Chapter 4. Anion–π
9/
3 and cation–π interactions in catalysis are discussed in Chapters 5 and 6,
0
1
0. respectively. Chapter 7 addresses the role of noncovalent interactions in the
1
oi: activity of dendrimers in catalysis. Noncovalent interactions in hydrogena-
d
g | tion and hydroformylation and in C–N coupling reactions are reported in
or Chapters 8 and 9, respectively, and asymmetric syntheses promoted by non-
c.
s.rs covalent interactions are discussed in Chapters 10, 11 and 12. Noncovalent
b
u interactions in Baeyer–Villiger reactions, redox catalysis and immobilization
p
s:// of catalysts on electrode surfaces are described in Chapters 13, 14 and 15,
p
htt respectively. Chapters 16 and 17 explain the role of noncovalent interac-
n
o tions in ionic liquids and their use in catalysis. The actions of these weak
9
01 forces in catalytic polymerization reactions are considered in Chapters 18
2
h and 19. Noncovalent interactions in metal–organic frameworks involved in
c
Mar catalytic transformations are delineated in Chapters 20, 21 and 22. Chapters
4 23 and 24 highlight the role of weak interactions in the adsorption of small
0
on molecules on immobilized amino acids and in biogenic impurities in alloys
d
he and segregated surfaces. Mechanochemical activation in catalysis and ion
s
bli pairing in the mechanism of Au(i) catalysts are highlighted in Chapters 25
u
P and 26, respectively. Noncovalent interactions in key metal-centred catalytic
intermediates, in biocatalysis and in understanding molecular reactivity are
discussed in Chapters 27, 28 and 29, respectively.
As reflected by the contents of this book, noncovalent interactions are
widely involved in catalytic transformations. We believe that this book will
provide a useful tool for readers interested in synthesis and catalysis, and
will open/inspire new directions in the field.
We would like to express our sincere gratitude to the authors of the chap-
ters for their valuable contributions. Dr Helen Armes and Connor Shep-
pard of the Royal Society of Chemistry are much appreciated for their kind
assistance.
Kamran T. Mahmudov
Maximilian N. Kopylovich
M. Fátima C. Guedes da Silva
Armando J. L. Pombeiro
Lisbon
9
0
0
P
F
90- Contents
4
6
1
0
8
8
7
1
8
7
9
9/
3
0
1
0. Chapter 1 Noncovalent Interactions in C–H Bond Functionalization 1
1
oi: Kamran T. Mahmudov, Atash V. Gurbanov, M. Fátima C.
d
g | Guedes da Silva and Armando J. L. Pombeiro
or
c.
s
s.r 1.1 Introduction 1
b
pu 1.2 C–H Bond Functionalization in Alkanes 5
s:// 1.3 C–H Bond Functionalization in Alkenes 8
p
htt 1.4 C–H Bond Functionalization in Alkynes 11
n
9 o 1.5 C–H Bond Functionalization in Aromatic
1
0 Compounds 13
2
ch 1.6 C–H Bond Functionalization in
ar
M Heterocyclic Compounds 16
4
0 1.7 C–H Bond Functionalization in
n
d o Aldehydes and Ketones 18
e
h 1.8 Conclusion 21
s
bli Acknowledgements 21
u
P
References 21
Chapter 2 Importance of C–H Hydrogen Bonding in Asymmetric
Catalysis 26
Satoru Arimitsu and Masahiro Higashi
2.1 Introduction 26
2.2 Historical Background of C–H Hydrogen Bonds 27
2.3 Computational Analysis of C–H Hydrogen
Bonds in Asymmetric Catalysis 31

Catalysis Series No. 36
Noncovalent Interactions in Catalysis
Edited by Kamran T. Mahmudov, Maximilian N. Kopylovich, M. Fátima C. Guedes da Silva and 
Armando J. L. Pombeiro
© The Royal Society of Chemistry 2019
Published by the Royal Society of Chemistry, www.rsc.org
ix
View Online
x Contents
2.4 Asymmetric Organometallic Catalysis
Controlled by C–H Hydrogen Bonding 34
2.5 Asymmetric Organocatalysis Controlled by
C–H Hydrogen Bonding 44
2.6 Conclusion 61
9
0
0 Acknowledgement 61
P
F
0- References 61
9
4
6
1
80 Chapter 3 Catalysis by Networks of Cooperative Hydrogen Bonds 66
8
17 José M. Saá, Victor J. Lillo and Javier Mansilla
8
7
9
9/
3 3.1 Introduction 66
0
1
0. 3.2 The Concept of Cooperativity 67
1
oi: 3.3 Hydrogen Bond Cooperativity 68
d
g | 3.3.1 σ and π Cooperative Hydrogen Bonds:
or Evidence 69
c.
s.rs 3.3.2 Networks of Cooperative Hydrogen Bonds
b
u (NCHBs) in Proton Transfer and
p
s:// Proton Transport 70
p
htt 3.4 Conclusion 85
n
o Acknowledgements 86
9
01 References 86
2
h
c
Mar Chapter 4 Secondary (Agostic Si–H/Electrostatic C–F)
4 Interactions in Alkaline Earth-based Catalysts 94
0
on Yann Sarazin and Jean-Francois Carpentier
d
e
h
s
bli 4.1 Introduction 94
u
P 4.2 Design of Alkaline Earth Precatalysts 96
4.2.1 General Considerations 96
4.2.2 Noncovalent Interactions for
Alkaline Earth Precatalysts 98
4.3 Alkaline Earth (Pre)catalyst Performance in
Catalysis 108
4.3.1 Catalysts and Precatalysts 108
4.3.2 Hydroamination Catalysis 110
4.3.3 Hydrophosphination Catalysis 112
4.3.4 Other Types of Catalysis 113
4.4 Conclusion 114
References 116
Chapter 5 Anion–π Catalysis 122
Rosa M. Gomila and Antonio Frontera
5.1 Introduction 122
5.2 Results and Discussion 123
5.2.1 Physical Nature of the Anion–π Interaction 123