Ball Milling Towards Green Synthesis: Applications, Projects, Challenges

Ball Milling Towards Green Synthesis Applications, Projects, Challenges RSC Green Chemistry

Editor-in-Chief: Professor James Clark, Department of Chemistry, University of York, UK

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Titles in the Series: 1: The Future of Glycerol: New Uses of a Versatile Raw Material 2: Alternative Solvents for Green Chemistry 3: Eco-Friendly Synthesis of Fine Chemicals 4: Sustainable Solutions for Modern Economies 5: Chemical Reactions and Processes under Flow Conditions 6: Radical Reactions in Aqueous Media 7: Aqueous Microwave Chemistry 8: The Future of Glycerol: 2nd Edition 9: Transportation Biofuels: Novel Pathways for the Production of Ethanol, Biogas and Biodiesel 10: Alternatives to Conventional Food Processing 11: Green Trends in Insect Control 12: A Handbook of Applied Biopolymer Technology: Synthesis, Degradation and Applications 13: Challenges in Green Analytical Chemistry 14: Advanced Oil Crop Biorefineries 15: Enantioselective Homogeneous Supported Catalysis 16: Natural Polymers Volume 1: Composites 17: Natural Polymers Volume 2: Nanocomposites 18: Integrated Forest Biorefineries 19: Sustainable Preparation of Metal Nanoparticles: Methods and Applications 20: Alternative Solvents for Green Chemistry: 2nd Edition 21: Natural Product Extraction: Principles and Applications 22: Element Recovery and Sustainability 23: Green Materials for Sustainable Water Remediation and Treatment 24: The Economic Utilisation of Food Co-Products 25: Biomass for Sustainable Applications: Pollution Remediation and Energy 26: From C-H to C-C Bonds: Cross-Dehydrogenative-Coupling 27: Renewable Resources for Biorefineries 28: Transition Metal Catalysis in Aerobic Alcohol Oxidation 29: Green Materials from Plant Oils 30: Polyhydroxyalkanoates (PHAs) Based Blends, Composites and Nanocomposites 31: Ball Milling Towards Green Synthesis: Applications, Projects, Challenges

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Ball Milling Towards Green Synthesis Applications, Projects, Challenges

Edited by

Brindaban Ranu University of Jadavpur, Jadavpur, Kolkata, India Email: [email protected]

Achim Stolle University of Jena, Jena, Germany Email: [email protected] RSC Green Chemistry No. 31

Print ISBN: 978-1-84973-945-0 PDF eISBN: 978-1-78262-198-0 ISSN: 1757-7039

A catalogue record for this book is available from the British Library r The Royal Society of Chemistry 2015

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For further information see our web site at www.rsc.org Foreword

Ball milling creates stress on substances. Solids break, and the resulting particles are modified in shape and size. Defects are induced and surface areas enlarged. Consequently, ball milling is highly relevant for various technological fields including mineral processing, materials engineering, and biomass degradation. In most of such applications the milling process is used for a particle size reduction. However, the energy induced by the mechanical treatment has other eﬀects as well. On the molecular level, for example, the arrangements of chemical structures can change leading to products with altered properties. The potential of such mechanochemical approaches and the implications in utilizing them in modern organic synthesis are nicely illustrated by the excellent contributions collected in the book edited by Stolle and Ranu. Many of the discussed reactions are solvent- free leading to ecological and economical advantages over existing tech- nologies providing the same products. Further benefits are recognized when comparing the energy eﬃciency of ball milling with other activation modes. Apparently, ball milling can be applied in a number of bond-forming processes, and various standard organic transformations (such as oxidations, reductions, and peptide formations) benefit from the use of this mechanochemical technique. Both low-molecular-weight compounds as well as polymers undergo specific chemical modifications in ball mills. Surprising observations have been made in both metal-catalyzed and organocatalytic C–C-bond formations including asymmetric versions thereof. Liquid-assisted grinding and kneading have proven advantageous for the preparation of coordination compounds. Being aware of the technological and process parameters is essential for achieving optimal results in synthetic transformations performed in ball mills. Although mechanochemical activations have already been utilized for a long time, the advantages of applying ball mills in targeted organic synthesis

RSC Green Chemistry No. 31 Ball Milling Towards Green Synthesis: Applications, Projects, Challenges Edited by Brindaban Ranu and Achim Stolle r The Royal Society of Chemistry 2015 Published by the Royal Society of Chemistry, www.rsc.org

vii viii Foreword has largely remained unrecognized until recently. The growing awareness of environmental implications of chemical processes and the search for greener solutions have led to a change, and today ball milling results are more present in the community than ever. Gaining a deeper understanding of the underlying mechanistic principles leading to mechanochemical activations and finding new reaction pathways resulting in products inacces- sible by other means will further expand the synthetic ball milling opportunities. This book will initiate new thought processes and promote the imple- mentation of ball milling as a modern synthetic technique in existing lab structures. Experts in academia and industry as well as interested new- comers will benefit from the timely presentations collected by Stolle and Ranu, and I congratulate both editors and authors for their stimulating contributions.

Carsten Bolm Aachen, Germany Preface

During the last few years ball milling has emerged as a powerful tool in eﬀecting various chemical reactions in a relatively green way by reducing the amount of solvent and operating at close to ambient temperature by application of mechanical energy. However, compared to other alternative forms of energy such as microwave and ultrasound, ball milling is still not familiar as a synthetic tool to a wide section of chemists and activity is limited to a comparatively small number of groups. Thus, the objective of this book is to create a general awareness of the importance of ball milling in chemical transformations among all section of readers including students, teachers and researchers. This book, entitled Ball Milling Towards Green Synthesis: Applications, Projects, Challenges, covers the current developments in the application of ball milling for various chemical transformations such as carbon–carbon and carbon–heteroatom bond formation, oxidation– reduction, organocatalytic reaction, dehydrogenative coupling, synthesis of peptide, polymeric materials, etc. highlighting its green aspects, scope and future prospects. This book also includes a chapter describing its origin, technological background and challenges. We gratefully acknowledge the co-operation from all those eminent and active scientists who contributed chapters to this book and the support and guidance from the staﬀ at the Royal Society of Chemistry. We hope this book will be able to provide basic information regarding ball milling and its application in chemical synthesis and thus will be useful to a wide section of chemists including students and researchers associated with academy and industry.

Brindaban C. Ranu Achim Stolle

Contents

Chapter 1 Carbon–Heteroatom Bond Forming Reactions and Heterocycle Synthesis under Ball Milling 1 Brindaban C. Ranu, Tanmay Chatterjee and Nirmalya Mukherjee

1.1 Introduction 1 1.2 Carbon–Heteroatom Bond Forming Reactions under Ball Milling 2 1.2.1 C–N Bond Forming Reactions 2 1.2.2 C–O Bond Forming Reactions 10 1.2.3 C–X (X ¼ F, Cl, I, SCN, OAc etc.) Bond Forming Reaction 11 1.2.4 C–X (X ¼ S, Se and Te) Bond Forming Reactions 12 1.3 Synthesis of Heterocycles 13 1.3.1 Nitrogen-containing Heterocycles 13 1.3.2 Oxygen-containing Heterocycles 18 1.3.3 Nitrogen–Oxygen-containing Heterocycles 22 1.3.4 Boron-containing Heterocycles 23 1.3.5 Fullerene Chemistry 25 1.3.6 Macrocycle Formation 27 1.4 Conclusion 31 References 31

Chapter 2 Carbon–Carbon Bond Forming by Ball Milling 34 Katharina Jacob, Robert Schmidt and Achim Stolle

2.1 Introduction 34 2.2 Cross-coupling Reactions 35 2.2.1 Sonogashira Cross-coupling 35

xi xii Contents 2.2.2 Suzuki–Miyaura Cross-coupling 36 2.2.3 Mizoroki–Heck Reaction 39 2.3 Homo-coupling Reactions 40 2.3.1 Homo-coupling of Phenols 40 2.3.2 Glaser Coupling 41 2.3.3 Homo-coupling of Boronic Acids 42 2.4 Miscellaneous 42 2.5 Carbon–Carbon Bond Formation by Condensation Reactions 43 2.5.1 Aldol-type Reactions 43 2.5.2 Knoevenagel Condensation 44 2.5.3 Michael Addition 46 2.5.4 Baylis–Hillman Reaction 49 2.5.5 Wittig Reaction 49 2.6 Diels–Alder Reaction 51 2.7 Grignard Reaction 52 2.8 McMurry Reactions 53 2.9 Further Miscellaneous Reactions 53 2.10 Summary 54 Abbreviations 54 References 55

Chapter 3 Oxidation and Reduction by Solid Oxidants and Reducing Agents using Ball-Milling 58 Giancarlo Cravotto and Emanuela Calcio Gaudino

3.1 Introduction 58 3.2 Mechanochemical Oxidation 60 3.3 Mechanochemical Reduction 73 3.4 Conclusion 78 References 79

Chapter 4 Asymmetric Organocatalytic Reactions under Ball Milling 81 Elizabeth Machuca and Eusebio Juaristi

4.1 Introduction 81 4.2 Asymmetric Organocatalysis and the Ball Milling Technique 82 4.2.1 Asymmetric Aldol Reaction 82 4.2.2 Asymmetric Michael Addition 85 4.2.3 Asymmetric Morita–Baylis–Hillman (MBH) Reaction 89 4.2.4 Asymmetric Alkylation of Imines 89 4.2.5 Desymmetrization of Aromatic Diamines and meso Anhydrides by Mechanochemistry 89 Contents xiii 4.3 Closing Remarks 90 Acknowledgements 91 References 91

Chapter 5 Cross Dehydrogenative Coupling Reactions by Ball Milling 96 Jingbo Yu, Zhijiang Jiang and Weike Su

5.1 Introduction 96 5.2 Cross Dehydrogenative Coupling Reactions under Ball Milling Conditions Applied to the Synthesis of Functionalized Tetrahydroisoquinolines 97 5.2.1 C(sp3)–C(sp3) Coupling Reaction 98 5.2.2 C(sp3)–C(sp) Coupling Reaction 98 5.2.3 C(sp3)–Aryl-C(sp2) Coupling Reaction 101 5.2.4 Milling Parameters 103 5.3 Asymmetric Cross-dehydrogenative Coupling Reaction by Ball Milling 106 5.3.1 Asymmetric Alkynylation of Prochiral C(sp3)–H Bonds 107 5.3.2 Effects on Enantioselectivity 109 5.4 Summary and Outlook 111 References 111

Chapter 6 Amino Acids and Peptides in Ball Milling 114 Thomas-Xavier Me´tro, Evelina Colacino, Jean Martinez and Fre´de´ric Lamaty

6.1 Introduction 114 6.2 Mechanochemical Synthesis and Derivatization of Amino Acids 117 6.2.1 Synthesis of Amino Acid Derivatives 117 6.2.2 Oxidation Reactions 117 6.2.3 Asymmetric Synthesis of Amino Acids 119 6.2.4 Synthesis of Unsaturated Amino Acids 121 6.2.5 Synthesis of Protected Amino Acids 123 6.3 Mechanosynthesis of Peptides 130 6.3.1 Synthesis of Di- and Tripeptides 130 6.3.2 Scale-up of Peptide Synthesis 131 6.3.3 Synthesis of a,b- and b,b-Dipeptides 133 6.3.4 Synthesis of Peptides with a Longer Amino Acid Sequence 137 6.4 Conclusion 148 References 148 xiv Contents Chapter 7 Ball-milling Mechanochemical Synthesis of Coordination Bonds: Discrete Units, Polymers and Porous Materials 151 Tomislav Frisˇˇcic´

7.1 Introduction 151 7.2 Benefits of Mechanochemical Synthesis in making Coordination Bonds 152 7.3 Methods for the Mechanosynthesis of Coordination Bonds 155 7.3.1 Neat Grinding 155 7.3.2 Grinding–Annealing 156 7.3.3 Liquid-assisted Grinding and Kneading 156 7.3.4 Ion- and Liquid-assisted Grinding (ILAG) 159 7.4 Characterization of Mechanochemical Products 160 7.5 Synthetic Strategies 161 7.5.1 Ligand Addition Reactions 161 7.5.2 Ligand Exchange 163 7.5.3 Acid–Base Reactions 164 7.5.4 Synthesis of Coordination Polymers and MOFs from Metal Oxides and Carbonates 165 7.5.5 Mechanochemical Dehydration 167 7.5.6 One-pot Multi-component Strategies 167 7.6 Functional Metal–Organic Materials 169 7.6.1 Microporous Metal–Organic Frameworks 169 7.6.2 Pharmaceutical Derivatives and Metallodrugs 171 7.6.3 Luminescent Materials 174 7.7 New Properties and Synthetic Opportunities arising from Mechanochemical Synthesis of Metal–Organic Materials 175 7.7.1 Structural Dynamics under Mechanochemical Conditions 175 7.7.2 Synthesis of Solid Solutions 177 7.7.3 Binding of Carbon Dioxide upon Mechanochemical Treatment 178 7.8 Mechanistic Studies of Mechanochemical MOF Synthesis 178 7.8.1 Stepwise Analysis 178 7.8.2 In Situ and Real-time Studies 180 7.8.3 Electron Microscopy 183 7.9 Outlook 183 Abbreviations 184 Acknowledgements 185 References 185