Sustainable Synthesis of Pharmaceuticals: Using Transition Metal Complexes as Catalysts (Green Chemistry) - Hardcover

Hardcover

ISBN 10: 1782629343 ISBN 13: 9781782629344

Verlag: Royal Society of Chemistry, 2018

Inhaltsangabe

There is a growing interest in the development of sustainable processes for the synthesis of pharmaceuticals and this book bridges the divide between industrial examples and the fundamental chemistry. It explains the basic principles of using transition metal catalysis with several green approaches for the synthesis of pharmaceuticals. Written by leading experts in the field, it provides a valuable and easy tool for scientists and industrialists who require information regarding this topic.

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Über die Autorin bzw. den Autor

James H Clark is Professor of Chemistry and Director of the Green Chemistry Centre of Excellence, The University of York, UK. He has led the green chemistry movement in Europe for the last 15 years and was the first scientific editor of the journal Green Chemistry and is Editor-in-chief of the RSC Green Chemistry book series. James H Clark is Professor of Chemistry and Director of the Green Chemistry Centre of Excellence, The University of York, UK. He has led the green chemistry movement in Europe for the last 15 years and was the first scientific editor of the journal Green Chemistry and is Editor-in-chief of the RSC Green Chemistry book series. University of Coimbra, Portugal Instituto de Tecnologia Química e Biológica, Portugal University of Lisbon, Portugal Universidade Federal de Minas Gerais, Brazil Louisiana State University, U.S.A.

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There is a growing interest in the development of sustainable processes for the synthesis of pharmaceuticals and this book bridges the divide between industrial examples and the fundamental chemistry. It explains the basic principles of using transition metal catalysis with several green approaches for the synthesis of pharmaceuticals. The topic is an important one for green chemistry and the chapters in this book on hydroformylation, green oxidation and olefin metathesis will also be of interest to both medicinal and organic chemists.
Written by leading experts in the field, it provides a valuable and easy tool for scientists and industrialists who require information regarding this topic.

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Sustainable Synthesis of Pharmaceuticals

Using Transition Metal Complexes as Catalysts

By Mariette M. Pereira, Mário J. F. Calvete

The Royal Society of Chemistry

Copyright © 2018 The Royal Society of Chemistry
All rights reserved.

ISBN: 978-1-78262-934-4

Contents

Chapter 1 Introduction M. M. Pereira and M. J. F. Calvete, 1, 
Chapter 2 Transition Metals in Greener Pharmaceutical Chemistry J. H. Clark, 5, 
Chapter 3 Sustainable Synthesis of Pharmaceuticals Using Alternative Techniques: Microwave, Sonochemistry and Mechanochemistry M. Pineiro and M. J. F. Calvete, 8, 
Chapter 4 Carbonylation Reactions in the Synthesis of Pharmaceutically Active Compounds R. Skoda-Földes and L. Kollár, 40, 
Chapter 5 Applications of Catalytic Hydroformylation in the Synthesis of Biologically Relevant Synthons and Drugs M. M. Pereira, 66, 
Chapter 6 Transfer Hydrogenation with Non-toxic Metals for Drug Synthesis B. Royo, 105, 
Chapter 7 Green Metal-catalysed Synthesis of Pharmaceutically Useful Asymmetric Epoxides and Sulfoxides C. C. Romão, 139, 
Chapter 8 C-C Bond Formation in the Sustainable Synthesis of Pharmaceuticals L. M. D. R. S. Martins, A. M. F. Phillips and A. J. L. Pombeiro, 193, 
Chapter 9 Metal-catalysed Metathesis Reactions for Greener Synthon/Drug Synthesis E. N. dos Santos, A. V. Granato and A. G. Santos, 230, 
Chapter 10 Tetravalent Boron-based Therapeutics Q. Meng, M. Wang and M. G. H. Vicente, 253, 
Subject Index, 282, 

CHAPTER 1

Introduction

M. M. PEREIRA AND M. J. F. CALVETE

University of Coimbra, CQC, Department of Chemistry, Rua Larga, Coimbra 3004-535, Portugal

1.1 Introduction

The development of sustainable processes for the synthesis of new active pharmaceutical ingredients (API) continues to be one of the great challenges for medicinal chemistry at universities and in the pharmaceutical industry. Given the benefits to public health, for decades, the pharmaceutical industry was more concerned with the end product than with the means of producing it. For decades, the synthetic methods of pharmaceutical products were the ones that led to greater waste and those that least respected the principles of green chemistry (green chemistry preferentially utilizes raw materials, avoids toxic and hazardous reagents and solvents, eliminates waste and when possible reduces the energy consumption, Chapter 3). However, in the last decade several companies have decided to adhere to the philosophy of green chemistry by modifying their production processes and especially by designing new processes where metrics (Chapter 3) have already been taken into account and the principles of waste and solvent reduction have been considered very important issues for the development of new API process development.

A key feature for improving the sustainability of the pharmaceutical industry is the design of new processes according to the principles of green chemistry. In the last few decades several companies changed their practices and adhered in particular to principle number 9: "catalytic reagents (as selective as possible) are superior to stoichiometric reagents". Nowadays, it has become clear to the pharmaceutical industry that the substitution of stoichiometric chemical reactions by catalytic processes may solve several industrial problems: (i) increasing selectivity for the desired product, particularly as regards the synthesis of enantiomerically pure pharmaceuticals; (ii) reducing the costs due to lower energy consumption; and (iii) reducing solvents and the overall process cost.

The great relevance of the use of organometallic reagents as catalysts for organic synthesis is clearly evidenced by the attribution of several Nobel Prizes in the field.

This book is aimed at researchers or post-graduate students, both in academia and the pharmaceutical industry, who are interested in developing processes for synthesis of drug synthons or APIs, using transition metals catalysts as the tool for achieving green chemistry purposes. As Clark reports in Chapter 2, the substitution of toxic metals by less toxic ones like iron and the development of new processes for recovering catalysts is clearly a new paradigm that the pharmaceutical industry should consider when introducing metals as catalysts for the development of new drugs. This issue is focused on in the great majority of the chapters.

In Chapter 2, J. Clark elucidates on the availability of critical chemical elements, mostly metals, and the strong discouragement of their use since there is a growing appreciation that not only are resources limited, but also their recovery is very difficult, and this vital part of sustainability must be recognized within green chemistry. It is crucial that efforts are increased both to use less metals and to design catalysts and processes to maximize recovery of the metals. Heterogeneous catalysts can definitely play a major role in this endeavour.

In Chapter 3, M. Pineiro and M. Calvete discuss the success of the philosophy and principles of green chemistry in the active search for more sustainable drug synthesis processes. A collection of diverse approaches has been reported so far, including the use of alternative reaction media and alternative technologies, such as microwaves, mechanochemistry, and ultrasound, especially when combined with new catalysts and catalytic systems, where the sustainability "improvement" is measured and quantified by using green chemistry metrics integrated in the drug discovery and development process in the pharmaceutical industry.

In Chapter 4, R. Skoda-Földes and L. Kollár shed light on pharmaceuticals arising from one-pot carbonylation processes, as typically the production of pharmaceuticals usually involves multistep syntheses where the selectivity and yield of the individual steps are of utmost importance. Among highly efficient catalytic processes, carbonylation received special attention as it involves both new carbon–carbon bond formation and the introduction of a synthetically useful functionality in the synthesis of carbonyl compounds and carboxylic acid derivatives. To achieve widespread application, more efficient catalysts should be developed that ensure higher turnover numbers and make it possible to carry out carbonylations at atmospheric conditions as well as to replace the starting material aryl iodides with cheaper bromides or, still preferably, chlorides. This reaction was described as a greener approach to prepare pharmaceuticals or their precursors bearing carboxylic acids, amides or esters functionalities in just one-pot.

In Chapter 5, M. Pereira highlights several aspects concerning the mechanism of rhodium-catalysed hydroformylation (still considered the "metal of choice" owing to its high activity and selectivity), the development and evolution of new metal catalysts and phosphorus ligands from a historical perspective, some strategies related to the synthesis of reusable catalysts for use in alternative media and the utilization of less toxic solvents and alternative metals. A set of selected examples for the direct transformations of olefins into aldehydes, via one-step 100% atom economy process, for the sustainable preparation of pharmaceutical intermediates or APIs is also described.

In Chapter 6, B. Royo describes the application of metal-catalysed asymmetric transfer hydrogenation and borrowing hydrogen processes to the synthesis of pharmaceuticals, especially those using Earth-abundant catalysts, which can replace precious...

Details zur Ausgabe

• Verlag: Royal Society of Chemistry
• Erscheinungsdatum: 2018
• Sprache: Englisch
• ISBN 10: 1782629343
• ISBN 13: 9781782629344
• Einband: Gebundene Ausgabe
• Anzahl der Seiten: 286
• Herausgeber: Pereira Mariette M, Calvete Mário J F
• Kontakt zum Hersteller: Nicht verfügbar
• Verantwortliche Person: gpsr@libri.de; gpsr@libri.de; ; Friedensallee 273; Hamburg; 22763; Deutschland