Table of Contents

Cover

1 Organic Sonochemistry: Ultrasound in Green Organic Synthesis

1.1. Introduction: history of ultrasound, organic sonochemistry and early work
1.2. Some elements of ultrasound theory
1.3. Laboratory and industrial equipment
1.4. Green organic sonochemistry
1.5. Sonochemistry in unconventional environments
1.6. Conclusion
1.7. References

2 High-Pressure Synthesis: An Eco-friendly Chemistry

2.1. High pressures in synthetic chemistry
2.2. Important concepts
2.3. Instrumentation
2.4. Applications
2.5. Conclusion
2.6. References

List of Authors

Index

End User License Agreement

List of Illustrations

Chapter 1

Figure 1.1. Hypotheses of the mechanism of the sonolysis of haloalkanes
Figure 1.2. Hypothesis of the mechanism of transformation of dibutyl sulfide und...
Figure 1.3. Study of the sonolysis of organic compounds at a frequency of 800 kH...
Figure 1.4. Study of sonolysis products of 9 amino acids at a frequency of 800 k...
Figure 1.5. Reduction of α,α′-dibromoketones in acetic acid by mercury dispersed...
Figure 1.6. Coordination of mercury with the enolate anion
Figure 1.7. Proposed mechanism of the reduction of α,α’-dibromoketones by ultras...
Figure 1.8. Saponification of aromatic carboxylic acid esters under ultrasonic i...
Figure 1.9. Barbier reaction under ultrasonic irradiation
Figure 1.10. Propagation of a sound wave in a liquid medium. For a color version...
Figure 1.11. Scale of sounds as a function of frequency
Figure 1.12. Simplified representation of the acoustic cavitation phenomenon. Fo...
Figure 1.13. Different ultrasonic baths: (a) single-frequency bath; (b) single-f...
Figure 1.14. Ultrasonic probes (source: with the kind permission of SinapTec): (...
Figure 1.15. High frequency reactor. For a color version of this figure, see www...
Figure 1.16. Cup-horn reactor. For a color version of this figure, see www.iste....
Figure 1.17. Continuous reactor
Figure 1.18. Chemical reaction sites in an aqueous medium subjected to acoustic ...
Figure 1.19. β-elimination of β-bromoacetals in heterogeneous media
Figure 1.20. Ultrasound-assisted Bouveault reaction
Figure 1.21. Ultrasound-assisted bromination reaction of anisole
Figure 1.22. Condensation reaction between a benzaldehyde and acetophenone
Figure 1.23. Ultrasound-assisted reaction of Knoevenagel between benzaldehyde an...
Figure 1.24. Ultrasonic benzoin condensation reaction catalyzed by octylmethylim...
Figure 1.25. Proposed mechanism for the ultrasound-assisted oxidation of primary...
Figure 1.26. Example of an ultrasound-assisted oxidation reaction with supported...
Figure 1.27. Oxidative depolymerization reaction of lignin
Figure 1.28. Epoxidation of chalcones under ultrasonic activation
Figure 1.29. Epoxidation reaction of cyclooctene under ultrasonic irradiation
Figure 1.30. Reduction reaction of benzophenone under ultrasonic irradiation
Figure 1.31. Ultrasound-assisted reduction reaction of nitro-aryls to amino-aryl...
Figure 1.32. Example of reduction of double bond under ultrasonic irradiation
Figure 1.33. Reduction of (2-nitro)ethylbenzene to 2-phenylethan-1-amine
Figure 1.34. Synthesis of pyrrole under ultrasonic irradiation
Figure 1.35. Ultrasound-assisted synthesis of 1,2,3-triazoles in the presence of...
Figure 1.36. Ultrasound-assisted condensation reaction between naphthols and ald...
Figure 1.37. Example of solvent-free ultrasonic synthesis of arylcoumarin under ...
Figure 1.38. Examples of anions and cations common in ionic liquid chemistry
Figure 1.39. Synthesis of [C₈MIM][OTf] without solvent and under ultrasonic irra...
Figure 1.40. Proposed mechanism for ultrasound-assisted oxidation of benzyl alco...
Figure 1.41. Ultrasound-assisted Heck reaction in ionic liquids based on imidazo...
Figure 1.42. Synthesis without a catalyst and in water of heterocycles via the a...
Figure 1.43. Basic hydrolysis of benzonitrile under ultrasonic activation
Figure 1.44. Hydrolysis of esters under ultrasonic irradiation
Figure 1.45. Ultrasound-assisted transesterification of mangiferin, troxerutin a...
Figure 1.46. Enantiospecific biocatalytic reduction of HPMAE to (R)-phenylephrin...
Figure 1.47. Biocatalyzed one-pot synthesis of indolizines by cyclo-addition

Chapter 2

Figure 2.1. Pressures encountered in the universe
Figure 2.2. If V_A + V_B > V^‡ > V_AB, then the reaction is accelerated under pressu...
Figure 2.3. Graphical representation of the activation volume V^‡
Figure 2.4. Reaction rates as a function of pressure
Figure 2.5. Typical diagram of the piston-cylinder equipment
Figure 2.6. Typical diagram of the sealing system
Figure 2.7. Typical diagram of Teflon reactors used under pressure
Figure 2.8. Diels-Alder cycloaddition involving a pyrrole under high pressure. S...
Figure 2.9. Diels-Alder cycloaddition involving a benzofuran under high pressure
Figure 2.10. Diels-Alder cycloaddition involving a tetrasubstituted dienophile u...
Figure 2.11. Functionalization of gold nanoparticles by cycloaddition (4+2)
Figure 2.12. Intramolecular [4+2] cycloaddition promoted under high pressure
Figure 2.13. Organocatalyzed heterodiels-Diels-Alder reaction under high pressur...
Figure 2.14. Hetero-Diels-Alder reaction catalyzed by a Lewis acid under high pr...
Figure 2.15. Cycloadditions (3+2) between a nitrone or azide and a dipolarophili...
Figure 2.16. (3+2) Annulation between a cyclopropane diester and a tetrasubstitu...
Figure 2.17. Cycloaddition (2+2) of an isocyanate and an enol ether under high p...
Figure 2.18. Multi-component (4+2)/(3+2) high-pressure cycloaddition
Figure 2.19. Creation of vicinal quaternary centers by Michael addition under hi...
Figure 2.20. Organocatalyzed desymmetrization of cyclohexadienones
Figure 2.21. Double addition of nitromethane anion to β,β–disubstituted Michael ...
Figure 2.22. Enantioselective organocatalyzed conjugate addition of nitromethane...
Figure 2.23. Organocalatyzed conjugate addition of enamines on Michael acceptors...
Figure 2.24. Conjugate addition of chiral imines to pressurized crotonates
Figure 2.25. Conjugate addition of anilines under pressure in the presence of he...
Figure 2.26. Baylis-Hillman reaction under high pressure
Figure 2.27. Oxy-Michael reaction under pressure
Figure 2.28. Addition of indoles to trifluoromethyl ketones under high pressure....
Figure 2.29. Organocatalyzed aldolization reaction under pressure
Figure 2.30. Organocatalytic Mannich reaction involving acetone under pressure
Figure 2.31. Strecker reaction of acetone and aniline under pressure
Figure 2.32. Dissymmetric urea formation under high pressure
Figure 2.33. Transesterification of hindered esters under high pressure
Figure 2.34. Cyanation of acetals under high pressure in nitromethane

Eco-compatibility of Organic Synthesis Set

coordinated by

Max Malacria

Volume 2

Activation Methods

Sonochemistry and High Pressure

Edited by

Jean-Philippe Goddard

Max Malacria

Cyril Ollivier

First published 2019 in Great Britain and the United States by ISTE Ltd and John Wiley & Sons, Inc.

Apart from any fair dealing for the purposes of research or private study, or criticism or review, as permitted under the Copyright, Designs and Patents Act 1988, this publication may only be reproduced, stored or transmitted, in any form or by any means, with the prior permission in writing of the publishers, or in the case of reprographic reproduction in accordance with the terms and licenses issued by the CLA. Enquiries concerning reproduction outside these terms should be sent to the publishers at the undermentioned address:

ISTE Ltd

27-37 St George’s Road

London SW19 4EU

www.iste.co.uk

John Wiley & Sons, Inc.

111 River Street

Hoboken, NJ 07030

USA

www.wiley.com

The rights of Jean-Philippe Goddard, Max Malacria and Cyril Ollivier to be identified as the authors of this work have been asserted by them in accordance with the Copyright, Designs and Patents Act 1988.

Library of Congress Control Number: 2019948627

British Library Cataloguing-in-Publication Data

A CIP record for this book is available from the British Library

ISBN 978-1-78630-510-7