Microwaves in Organic Synthesis

Antonio de la Hoz, André Loupy

• Publisher: Wiley-VCH
• Year: 2013
• Print ISBN:
  9783527331161
• eBook ISBN:
  9783527651337
• Edition: 3
• Topic: Physical Sciences
• Subtopic: Organic Chemistry

The third edition of the bestselling two-volume reference covers everything you need to know about microwave technology for synthesis
- from the best equipment to nonthermal effects, from solid-support reactions to catalysis. Completely revised and updated with half of the authors completely new to the project, this comprehensive work is clearly divided into two parts on the fundamentals of microwave irradiation, and application of microwaves and synergies with other enabling techniques. Also new to this edition are chapters on on-line monitoring, flow chemistry, combination with ultrasounds and natural products, including multicomponent reactions.

An indispensable source for organic, catalytic, physical, and medicinal chemists.

Contents to Volume 1

Preface

Since the publication of the first edition of this book in 2002, the use of microwaves in organic synthesis has today become a general and useful methodology, with application in almost all kinds of reactions in organic chemistry and also in many other fields of chemistry, not covered in this book.

The two famous pioneering papers from Gedye and Giguere in 1986 are generally considered the beginning of the use of this methodology in organic synthesis. Since then, many authors have contributed to its development and spreading throughout the world. We would highlight the pioneering work of Strauss in Australia, Loupy/Bram and Hamelin in Europe, and Varma in the USA – all of them authors in the present and previous editions of this book. Today, a new generation of very active and highly competent chemists has extended the applications of microwave irradiation and the development of new instruments and methodologies.

The introduction of microwave instruments specially designed for chemistry was one of the milestones in the development of this methodology. Since their introduction, the number of papers dedicated to microwave-assisted organic chemistry has increased exponentially. Thanks to these instruments, careful control of all reaction parameters, temperature, pressure, incident power, and so on, is now possible. In this way, reproducibility of microwave-assisted reactions, the major drawback of this methodology when using domestic-type ovens, was achieved. Moreover, these new instruments were fitted for laboratory work with high security.

This third edition consists of 25 chapters seriously restructured and updated in relation to the previous editions, nine chapters being completely new.

The first part of the book is dedicated to fundamental aspects of microwave irradiation in organic synthesis. First, a revision and description of materials–wave interactions is presented (Chapter 1), including interactions from molecules to macromolecules to solids and colloidal suspensions. Chapter 2 is dedicated to microwave technology and instruments including scale-up, while Chapter 3 is dedicated to the design of microwave-assisted processes. The issue of microwave effects (possibly nonthermal) is discussed in Chapter 4; methods, theories, and predictive models are collected in a new chapter (Chapter 6). The modifications of selectivity under microwave irradiation are reviewed in Chapter 5. Some important aspects of microwave methodology are collected in the new Chapters 7–9 such as the use of microwave susceptors (Chapter 7), methods for monitoring of microwave-assisted reactions (Chapter 8), and the influence of variable frequency in organic chemistry (Chapter 9).

The second part is dedicated to applications of microwave irradiation and its synergic use with other enabling technologies. In this regard, new chapters have been included on microwaves and electrochemistry (Chapter 12), ultrasound (Chapter 13), and flow methodologies (Chapter 25). Revised chapters were prepared on reactions on solid supports (Chapter 10) and photochemistry and photocatalysis under microwaves (Chapter 14). Some classic applications, in which microwave irradiation has afforded spectacular results, have been revised and extended, such as transition metal-catalyzed reactions (Chapter 15), heterocyclic chemistry (Chapter 16), cycloaddition reactions (Chapter 17), carbohydrate chemistry (Chapter 21), and multicomponent reactions (Chapter 24). Applications to solid-phase peptide synthesis (Chapter 20), polymer chemistry (Chapter 22), and carbon nanostructured materials (Chapter 23) have been substantially modified since these very active areas have found many new applications. Finally, new chapters dealing with applications to gaseous reagents (Chapter 11), heterogeneous catalysis (Chapter 18), and the synthesis of natural products (Chapter 19) have been added.

We wish to thank sincerely all our colleagues and friends involved in the realization of this book. We want to express sincerely to them, all eminent specialists, our gratitude for agreeing to devote their competence and time to submitting and reviewing chapters to ensure the success of this book.

We would like especially to dedicate this book to the memory two authors in the first and second editions recently deceased: Professor Jack Hamelin, our “Jack Pote” (in French, pote means friend), and Mohamed Soufiaoui, our “Great Friend.” Chapters 16 and 17 are dedicated to them. They were excellent friends as well as extraordinary researchers with important dedication and engagement with their respective universities and countries (France and Morocco).

Antonio de la Hoz and André Loupy

List of Contributors

Jesus Alcázar

Janssen-Cilag SA

Janssen Research and Development

C/Jarama 75

45007 Toledo

Spain

R.B. Nasir Baig

US Environmental Protection Agency

Sustainable Technology Division

National Risk Management Research Laboratory

26 West Martin Luther King Drive

Cincinnati

OH 45268

USA

Alina Mariana Balu

Universidad de Córdoba

Departamento de Química Orgánica

Campus de Excelencia Agroalimentario de Rabanales (CeiA3) Edificio Marie Curie

Carretera Nacional IV-A

Km 396

Córdoba 14014

Spain

Jitender B. Bariwal

ISF College of Pharmacy

Department of Medicinal Chemistry

Ferozepur G.T. Road

Moga

Punjab 142001

India

Jean Pierre Bazureau

Université de Rennes 1

Sciences Chimiques de Rennes

UMR CNRS 6226

Groupe Ingenierie Chimique et Molecules pour le Vivant (ICMV)

35042 Rennes

France

Rachid Benhida

Université de Nice–Sophia Antipolis

UMR 7272 CNRS

Equipe Molécules Bioactives

Institut de Chimie de Nice

28 avenue de Valrose

06108 Nice cedex 2

France

Thierry ...

Table of contents

• Cover
• Related Titles
• Title Page
• Copyright
• Contents to Volume 1
• Preface
• List of Contributors
• Part I: Fundamental Aspects of Microwave Irradiation in Organic Chemistry
• Part II: Applications of Microwave Irradiation
• Contents to Volume 2
• Preface
• List of Contributors
• Chapter 15: Microwave-Heated Transition Metal-Catalyzed Coupling Reactions
• Chapter 16: Microwaves in Heterocyclic Chemistry
• Chapter 17: Microwave-Assisted Cycloaddition Reactions
• Chapter 18: Microwave-Assisted Heterogeneously Catalyzed Processes
• Chapter 19: Microwaves in the Synthesis of Natural Products
• Chapter 20: Microwave-Enhanced Synthesis of Peptides, Proteins, and Peptidomimetics
• Chapter 21: A Journey into Recent Microwave-Assisted Carbohydrate Chemistry
• Chapter 22: Polymer Chemistry Under Microwave Irradiation
• Chapter 23: Application of Microwave Irradiation in Carbon Nanostructures
• Chapter 24: Microwave-Assisted Multicomponent Reactions in the Synthesis of Heterocycles
• Chapter 25: Microwave-Assisted Continuous Flow Organic Synthesis (MACOS)
• Index