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Metal-Catalyzed Cross-Coupling Reactions. Two completely revised and enlarged edition. Edited by Armin de Meijere and Franois Diederich

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Angewandte
Books
Chemie
Metal-Catalyzed Cross-Coupling
Reactions
Two completely
revised and
enlarged edition.
Edited by Armin
de Meijere and
Franois Diederich.
Wiley-VCH, Weinheim 2004.
916 pp., hardcover
E 329.00.—ISBN
3–527–30518–1
Just as Technicolor changed the movies,
so has cross-coupling chemistry enriched
organic synthesis. Cross-coupling reactions, which are transition-metal-catalyzed coupling reactions of organometallic compounds with organic halides or
related electrophiles, are arguably some
of the most important reactions of
organic chemistry. Is the exploratory
phase over, and have we reached the
optimization phase? Probably not! In
the last few years, fundamentally new
classes of ligands and reactions of great
synthetic value have been developed.
Sterically demanding phosphine and Nheterocyclic carbene ligands, the Hartwig–Buchwald amination, iron-catalyzed
cross-couplings, and the coupling of sp3
carbon atoms, have only recently
moved into synthetic laboratories.
The first edition of this work, published in 1998 with a healthy 540 pages,
has become one of the most popular
books on cross-coupling reactions. The
appearance of a completely revised
and enlarged second edition, consisting
of two volumes, is an indication of the
rapidly growing interest in cross-coupling chemistry.
Angew. Chem. Int. Ed. 2005, 44, 1157 – 1159
There is no best actor, but only a
good cast for a certain play, and the
same is true for cross-coupling reactions.
Each method has its advantages and disadvantages, and the best choice for a
particular transformation depends on
many criteria. Desirable preconditions
are commercial availability of the starting materials, reagents, and catalysts, a
high yield under mild reaction conditions, high atom economy with minimal
formation of side-products, wide applicability and functional group tolerance,
stability of products under the reaction
conditions, and low toxicity of all compounds involved. The book deals with
all of these aspects, and provides the
reader with a good grasp of the field.
In 15 well-written chapters, renowned
experts such as Bckvall, Brse, Buchwald, Denmark, Echavarren, Haley,
Kazmaier, Knochel, Marek, de Meijere,
Mitchell, Miyaura, Negishi, Snieckus,
and Tsuji discuss the most relevant
developments in cross-coupling chemistry and illustrate them with examples.
Each chapter provides the reader with
background information, discusses the
latest developments, and ends with representative experimental procedures
for the reactions that were described.
However, the user-friendliness could
be further improved by indicating in
the main text whether the description
of a reaction is followed at the end by
an experimental procedure.
In the first chapter, important mechanistic aspects of cross-coupling reactions
are discussed, a good warm-up for the
remainder of the book. Five chapters
deal with key players in cross-coupling
chemistry: the various organoboron, -tin,
-silicon, -zinc, and -magnesium reagents.
In addition, other groundbreaking
classics such as the Heck reaction,
cross-coupling reactions to sp carbon
atoms (e.g., the Sonogashira reaction),
carbometalations, reactions of p-allyl
intermediates (e.g., the allylic alkylation), and also reactions to form bonds
between nitrogen and aromatic carbon
atoms (the Hartwig–Buchwald amination) are refreshingly presented. Three
more chapters deal with 1,4-addition to
conjugated dienes, the palladium-catalyzed coupling of propargyl compounds,
and directed ortho-metalation.
A final highlight is the chapter on
the Negishi coupling, which gives an
www.angewandte.org
insight into the historic relationship of
the different cross-coupling reactions.
This chapter also discusses the advantages and disadvantages of the different
types of reactions.
This book is not meant to be a comprehensive encyclopedia. In fact, for the
sake of time-pressed readers, the editors
skillfully focus on the most important
aspects of modern cross-coupling
chemistry. All the chapters are of high
didactic value, are easily readable, and
present state-of-the-art science. Therefore, students as well as experienced
chemists in academia and industry will
benefit from this book, and it can be recommended unreservedly. This new edition represents much more than an
update. It is a reader-friendly definitive
book of cross-coupling chemistry!
Frank Glorius
Fachbereich Chemie
Philipps-Universitt Marburg (Germany)
DOI: 10.1002/anie.200485248
Experiments, Models, Paper Tools
Cultures of Organic
Chemistry in the
Nineteenth Century. By Ursula
Klein. Stanford University Press, Stanford 2003. 305 pp.,
hardcover
$ 65.00.—ISBN
0–8047–4359–2
Traditionally, historians, and philosophers of science have analyzed the
dynamics of discovery by taking into
account the experiments and theories
of a period, and setting these into the
context of particular social and economic conditions prevailing at the
time. Nevertheless, a few historians and
philosophers of science now maintain
that these time-honored approaches,
exemplified for the history of chemistry
by such canonical works as Partingtons
A History of Chemistry and Ihdes The
Development of Modern Chemistry, are
insufficient for a complete analysis.
2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1157
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