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Homogeneous Catalysis

Homogeneous Catalysis
Understanding the Art
by

Piet W.N.M. van Leeuwen
University of Amsterdam,
Amsterdam, The Netherlands

KLUWER ACADEMIC PUBLISHERS
DORDRECHT / BOSTON / LONDON

A C.I.P. Catalogue record for this book is available from the Library of Congress.

ISBN 1-4020-3176-9 (PB)
ISBN 1-4020-1999-8 (HB)
ISBN 1-4020-2000-7 (e-book)

Published by Kluwer Academic Publishers,
P.O. Box 17, 3300 AA Dordrecht, The Netherlands.
Sold and distributed in North, Central and South America
by Kluwer Academic Publishers,
101 Philip Drive, Norwell, MA 02061, U.S.A.
In all other countries, sold and distributed
by Kluwer Academic Publishers,
P.O. Box 322, 3300 AH Dordrecht, The Netherlands.

Printed on acid-free paper

All Rights Reserved
© 2004 Kluwer Academic Publishers
No part of this work may be reproduced, stored in a retrieval system, or transmitted
in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or
otherwise, without written permission from the Publisher, with the exception
of any material supplied specifically for the purpose of being entered
and executed on a computer system, for exclusive use by the purchaser of the work.
Printed in the Netherlands.

Table of contents

Preface

xi

Acknowledgements
1.

xiii

INTRODUCTION

1
1
CATALYSIS
HOMOGENEOUS CATALYSIS
6
HISTORICAL NOTES ON HOMOGENEOUS CATALYSIS
7
8
CHARACTERISATION OF THE CATALYST
LIGAND EFFECTS
10
1.5.1
Phosphines and phosphites: electronic effects
10
1.5.2
Phosphines and phosphites: steric effects
12
1.5.3
Linear Free Energy Relationships
14
1.5.4
Phosphines and phosphites: bite angle effects
16
1.6
LIGANDS ACCORDING TO DONOR ATOMS
20
Anionic and neutral hydrocarbyl groups
20
1.6.1
1.6.2
Alkoxy and imido groups as anionic ligands
21
1.6.3
Amines, imines, oxazolines and related ligands
21
1.6.4
Phosphines, phosphites, phosphorus amides, phospholes
and related ligands
23
1.6.5
Carbenes, carbon monoxide
24
1.6.6
Common anions
25

1.1
1.2
1.3
1.4
1.5

v

vi
2.

Table of contents

ELEMENTARY STEPS

29

CREATION OF A “VACANT” SITE AND CO-ORDINATION OF THE
2.1
SUBSTRATE
29
30
2.2
INSERTION VERSUS MIGRATION
β-ELIMINATION AND DE-INSERTION
35
2.3
2.4
OXIDATIVE ADDITION
36
39
2.5
REDUCTIVE ELIMINATION
2.6
α-ELIMINATION REACTIONS
41
2.7
CYCLOADDITION REACTIONS INVOLVING A METAL
42
ACTIVATION OF A SUBSTRATE TOWARD NUCLEOPHILIC ATTACK
2.8
2.8.1
Alkenes
2.8.2
Alkynes
2.8.3
Carbon monoxide
2.8.4
Other substrates
2.9
σ-BOND METATHESIS
2.10 DIHYDR...
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