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Beschreibung

Presents state-of-the-art information concerning the syntheses of valuable functionalized organic compounds from alkanes, with a focus on simple, mild, and green catalytic processes Alkane Functionalization offers a comprehensive review of the state-of-the-art of catalytic functionalization of alkanes under mild and green conditions. Written by a team of leading experts on the topic, the book examines the latest research developments in the synthesis of valuable functionalized organic compounds from alkanes. The authors describe the various modes of interaction of alkanes with metal centres and examine theoxidative alkane functionalization upon C-O bond formation. They address the many types of mechanisms, discuss typical catalytic systems and highlight the strategies inspired by biological catalytic systems. The book also describes alkane functionalization upon C-heteroatom bond formation as well as oxidative and non-oxidative approaches. In addition, the book explores non-transition metal catalysts and metal-free catalytic systems and presents selected types of functionalization of sp3 C-H bonds pertaining to substrates other than alkanes. This important resource: * Presents a guide to the most recent advances concerning the syntheses of valuable functionalized organic compounds from alkanes * Contains information from leading experts on the topic * Offers information on the catalytic functionalization of alkanes that allows for improved simplicity and sustainability compared to current multi-stage industrial processes * Explores the challenges inherent with the application of alkanes as starting materials for syntheses of added value functionalized organic compounds Written for academic researchers and industrial scientists working in the fields of coordination chemistry, organometallic chemistry, catalysis, organic synthesis and green chemistry, Alkane Functionalization is an important resource for accessing the most up-to-date information available in the field of catalytic functionalization of alkanes.

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Veröffentlichungsjahr: 2018

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Alkane Functionalization

Edited by

Armando J. L. Pombeiro and M. Fátima C. Guedes da Silva

Instituto Superior TécnicoUniversidade de Lisboa, Portugal

Copyright

This edition first published 2019

© 2019 John Wiley & Sons Ltd

All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, except as permitted by law. Advice on how to obtain permission to reuse material from this title is available at http://www.wiley.com/go/permissions.

The right of Armando J. L. Pombeiro and M. Fátima C. Guedes da Silva to be identified as the authors of the editorial material in this work has been asserted in accordance with law.

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In view of ongoing research, equipment modifications, changes in governmental regulations, and the constant flow of information relating to the use of experimental reagents, equipment, and devices, the reader is urged to review and evaluate the information provided in the package insert or instructions for each chemical, piece of equipment, reagent, or device for, among other things, any changes in the instructions or indication of usage and for added warnings and precautions. While the publisher and authors have used their best efforts in preparing this work, they make no representations or warranties with respect to the accuracy or completeness of the contents of this work and specifically disclaim all warranties, including without limitation any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives, written sales materials or promotional statements for this work. The fact that an organization, website, or product is referred to in this work as a citation and/or potential source of further information does not mean that the publisher and authors endorse the information or services the organization, website, or product may provide or recommendations it may make. This work is sold with the understanding that the publisher is not engaged in rendering professional services. The advice and strategies contained herein may not be suitable for your situation. You should consult with a specialist where appropriate. Further, readers should be aware that websites listed in this work may have changed or disappeared between when this work was written and when it is read. Neither the publisher nor authors shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.

Library of Congress Cataloging‐in‐Publication Data applied for

ISBN: 9781119378808

Cover image: Courtesy of Armando J. L. Pombeiro and M. Fátima C. Guedes da Silva

Cover design by Wiley

List of Contributors

Mathieu Achard

Université de Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)

UMR 6226

Rennes

France

Seihwan Ahn

Department of Chemistry

KAIST and Center for Catalytic Hydrocarbon Functionalizations

Daejeon

South Korea

and

Center for Catalytic Hydrocarbon Functionalizations

Institute for Basic Science (IBS)

Daejeon

South Korea

Elisabete C.B.A. Alegria

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

and

Chemical Engineering Department

Instituto Superior de Engenharia de Lisboa

Instituto Politécnico de Lisboa

Lisboa

Portugal

Mu‐Hyun Baik

Department of Chemistry

KAIST and Center for Catalytic Hydrocarbon Functionalizations

Daejeon

South Korea

and

Center for Catalytic Hydrocarbon Functionalizations

Institute for Basic Science (IBS)

Daejeon

South Korea

Christian Bruneau

Université de Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)

UMR 6226

Rennes

France

Konstantin P. Bryliakov

Novosibirsk State University and Boreskov Institute of Catalysis

Novosibirsk

Russian Federation

Fabrizio Cavani

Dipartimento di Chimica Industriale “Toso Montanari”

Università di Bologna

Bologna

Italy

Sunney I. Chan

Institute of Chemistry

Academia Sinica

Sec. 2, Nankang

Taipei

Taiwan

and

Department of Chemistry

National Taiwan University

Sec. 4, Taipei

Taiwan

Evgeniy G. Chepaikin

Institute of Structural Macrokinetics and Materials Science

Russian Academy of Sciences

Chernogolovka

Moscow

Russia

Alessandro Chieregato

Dipartimento di Chimica Industriale “Toso Montanari”

Università di Bologna

Bologna

Italy

and

Current address:

Strategy Development Research Division

Catalysis Refining and Base Chemicals Department

TOTAL Research & Technology

Seneffe

Belgium

Miquel Costas

Departament de Química I Institut de Química Computacional i Catàlisi

Facultat de Ciències

Campus de Montilivi

Girona

Catalonia

Spain

Robert H. Crabtree

Yale Chemistry Department and Energy Sciences Institute

Yale University

Yale West Campus

West Haven CT USA

Bruno Dominelli

Molecular Catalysis

Technische Universität München (TUM)

Department of Chemistry/Catalysis Research Center

8 Garching bei München

Germany

Ana M. Faisca Phillips

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Huaquan Fang

State Key Laboratory of Organometallic Chemistry

Shanghai Institute of Organic Chemistry

Shanghai

China

Luís M. T. Frija

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Christian R. Goldsmith

Department of Chemistry and Biochemistry

Auburn University

179 Chemistry Building

Auburn

AL

United States

M. Fátima C. Guedes da Silva

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal.

Jianlin Han

School of Chemistry and Chemical Engineering

State Key Laboratory of Coordination Chemistry

Jiangsu Key Laboratory of Advanced Organic Materials

Nanjing University

Nanjing

People's Republic of China

Zheng Huang

State Key Laboratory of Organometallic Chemistry

Shanghai Institute of Organic Chemistry

Shanghai

China

Damodar Janmanchi

Institute of Chemistry

Academia Sinica

Sec. 2, Nankang

Taipei

Taiwan

Maximilian N. Kopylovich

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Fritz E. Kühn

Molecular Catalysis

Technische Universität München (TUM)

Department of Chemistry/Catalysis Research Center

8 Garching bei München

Germany

Maxim L. Kuznetsov

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Jay A. Labinger

Beckman Institute

California Institute of Technology

Pasadena

CA

USA

Osvaldo Lanzalunga

Dipartimento di Chimica

Università degli Studi di Roma “La Sapienza” and Istituto CNR di Metodologie Chimiche (IMC‐CNR)

Sezione Meccanismi di Reazione

Rome

Italy

Johannes A. Lercher

Department of Chemistry

Technische Universität München

Garching

Germany

Anja C. Lindhorst

Molecular Catalysis

Technische Universität München (TUM)

Department of Chemistry/Catalysis Research Center

8 Garching bei München

Germany

Chih‐Cheng Liu

Institute of Chemistry

Academia Sinica

Sec. 2, Nankang

Taipei

Taiwan

Guixia Liu

State Key Laboratory of Organometallic Chemistry

Shanghai Institute of Organic Chemistry

Shanghai

China

Oleg Y. Lyakin

Novosibirsk State University and Boreskov Institute of Catalysis

Novosibirsk

Russian Federation

Kamran T. Mahmudov

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

and

Department of Chemistry

Baku State University

Baku

Azerbaijan

Luísa M. D. R. S. Martins

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Dan Meyerstein

Chemical Sciences Department

Ariel University

Ariel

Israel

and

Ben‐Gurion University

Beer‐Sheva

Israel

Jean‐Marc M. Millet

Institut de Recherche sur la Catalyse et l'Environnement de Lyon

UMR 5256 Universite Claude‐Bernard Lyon 1

Villeurbanne Cedex

France

Daniel J. Mindiola

Department of Chemistry

University of Pennsylvania

Philadelphia PA

USA

Dmytro S. Nesterov

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Oksana V. Nesterova

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Jose Manuel Lopez Nieto

Instituto de Tecnologia Quimica

Universitat Politècnica de València‐Consejo Superior de Investigaciones Científicas

Valencia

Spain

Giorgio Olivo

Dipartimento di Chimica

Università degli Studi di Roma “La Sapienza” and Istituto CNR di Metodologie Chimiche (IMC‐CNR)

Sezione Meccanismi di Reazione

Rome

Italy

António Palavra

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Armando J. L. Pombeiro

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Ravirala Ramu

Institute of Chemistry

Academia Sinica

Sec. 2, Nankang

Taipei

Taiwan

Ana P.C. Ribeiro

Centro de Química Estrutural

Instituto Superior Técnico

Universidade de Lisboa

Lisboa

Portugal

Maricruz Sanchez‐Sanchez Department of Chemistry

Technische Universität München

Garching

Germany

Georgiy B. Shul'pin

Semenov Institute of Chemical Physics

Russian Academy of Sciences

Moscow