Ideas In Chemistry And Molecular Sciences: Advances In Synthetic Chemistry

Ideas in Chemistry and Molecular Sciences Edited by Bruno Pignataro Related Titles Nugent, Thomas C. (ed.) Pignataro, Bruno (ed.) Chiral Amine Synthesis Tomorrow’s Chemistry Today Methods, Developments and Applications Concepts in Nanoscience, Organic Materials and Environmental Chemistry 2nd edition 2010 ISBN: 978-3-527-32509-2 2009 ISBN: 978-3-527-32623-5 Boysen, Mike Martin Kwabena (ed.) Carbohydrates – Tools for Stereoselective Synthesis 2010 Carreira, E. M., Kvaerno, L. Classics in Stereoselective Synthesis ISBN: 978-3-527-32379-1 2009 ISBN: 978-3-527-29966-9 (Softcover) Pignataro, Bruno (ed.) Ideas in Chemistry and Molecular Sciences Where Chemistry Meets Life 2010 ISBN: 978-3-527-32541-2 ISBN: 978-3-527-32452-1 (Hardcover) ¨ Christmann, M., Brase, S. (eds.) Asymmetric Synthesis – The Essentials 2008 Softcover Pignataro, Bruno (ed.) Ideas in Chemistry and Molecular Sciences Advances in Nanotechnology, Materials and Devices 2010 ISBN: 978-3-527-32543-6 ISBN: 978-3-527-32093-6 Ideas in Chemistry and Molecular Sciences Advances in Synthetic Chemistry Edited by Bruno Pignataro The Editor Prof. Bruno Pignataro University of Palermo Department of Physical Chemistry Viale delle Scienze 90128 Palermo Italy All books published by Wiley-VCH are carefully produced. Nevertheless, authors, editors, and publisher do not warrant the information contained in these books, including this book, to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate. Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Bibliographic information published by the Deutsche Nationalbibliothek The Deutsche Nationalbibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data are available on the Internet at .  2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Cover Design Adam Design, Weinheim Typesetting Laserwords Private Limited, Chennai, India Printing and Binding betz-druck GmbH, Darmstadt Printed in the Federal Republic of Germany Printed on acid-free paper ISBN: 978-3-527-32539-9 Set ISBN: 978-3-527-32875-8 V Contents Preface XI List of Contributors Part I 1 1.1 1.2 1.3 1.3.1 1.4 1.4.1 1.5 1.5.1 1.5.2 1.5.3 1.5.4 1.5.5 1.5.6 1.5.7 1.5.8 1.5.9 1.5.10 1.5.11 1.6 XVII Innovative Processes in Organic Chemistry 1 N-Hydroxy Derivatives: Key Organocatalysts for the Selective Free Radical Aerobic Oxidation of Organic Compounds 3 Carlo Punta and Cristian Gambarotti Introduction 3 General Reactivity of N-Hydroxy Derivatives 3 Aerobic Oxidation Catalyzed by N-Hydroxy Amines 6 Aerobic Oxidation of Alcohols to Aldehydes and Ketones 6 Aerobic Oxidation Catalyzed by N-Hydroxy Amides 9 Peroxidation of Polyunsaturated Fatty Acids 9 Aerobic Oxidation Catalyzed by N-Hydroxy Imides 10 Oxidation of Benzylalcohols to Aldehydes 10 Oxidation of Silanes 12 Oxidation of N-Alkylamides 12 Oxidation of Tertiary Benzylamines to Aldehydes 13 Oxidative Functionalization of Alkylaromatics 14 Oxidative Acylation of N-Heteroaromatic Bases 15 Aerobic Synthesis of p-Hy