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Book Review A УHeckФ of a Lot of Chemistry Palladium Reagents and Catalysts. Innovations in Organic Synthesis. By J. Tsuji

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A “Heck” of a Lot of Chemistry
Palladium Reagents and Catalysts.
Innovations in Organic Synthesis. By
J. Tsuji. Wiley, Chichester, 3 995. 560
pp., hardcover E 125.00.-ISBN 0-47195483-7
Palladium is justifiably regarded as the
transition metal with the greatest variety
of potential applications in organic synthesis. Many different reactions are
catalyzed or initiated by palladium
complexes, and the
leading chemistry
journals contain articles reporting synthetic uses of palladium in almost
every issue. Because
of the continuing
flood of new publications in this area,
much time and effort is absorbed in keeping up with the latest developments. Thus
there was certainly a need for an up-todate monograph on palladium reagents in
organic synthesis.
The book by J. Tsuji fulfills this need in
exemplary style. Over 2500 literature references, extending up to the beginning of
1994, are treated under the relevant topic
areas with succinct commentaries, in a
way that ensures lucidity and ease of use
despite the vast amount of information.
The schemes showing the important reactions and mechanisms are clear and of a
high quality.
The subject index lists reagents, substrates, target molecules, and some named
reactions. Reactions of a particular type
can be found by using the contents list in
conjunction with following the systematic
arrangement of the subject matter. This
This section contains book reviews and a list of
new books received by the editor. Book reviews are
written by invitalion from the editor. Suggestions
for books to be reviewed and for book reviewers
are welcome. Publishers should send brochures o r
(better) books to the editorial office: Redaktion
Angewandte Chemie, Postfach 10 11 61, D-69451
Weinheim. Germany. T h e editor reserves the right
of selecting which books will be reviewed. Uninvited hooks not chosen for revicw will not be returned.
A n g w . Chem. lnt. Ed. Engl. 1996. 3S, No. 15
system is based on the mechanisms that
the reactions are assumed to involve according to current knowledge. It is a pragmatic and effective approach, although
one may occasionally question the assumptions, as there still remains much to
be learned about the mechanisms of palladium-catalyzed reactions.
The contents are arranged in five chapters of widely differing lengths. Chapter 1
(1 2 pp.) summarizes the fundamentals
and main features of palladium chemistry,
including the structures and properties of
some important (mostly commercially
available) palladium complexes and information about commonly used ligands.
Some basic reactions of palladium complexes are described, and the chapter ends
with a comprehensive list of references for
further reading. Chapter 2 consists of only
six pages, giving additional basic information about stoichiometric and catalytic reactions of palladium.
Chapter 3 is much longer (106 pp.), and
covers oxidative reactions using palladium(I1) compounds. After a short introduction (Section l ) , the Wacker process
and related reactions are described in Section 2. The following sections are devoted
to stoichiometric reactions of 71-ally1 complexes and to transformations of various
compounds (dienes. allenes, alkynes,
arenes, and many more) that are induced
or catalyzed by palladium(1r) compounds.
Chapter 4 is by far the longest (over 400
pp.) and deals with catalytic reactions of
palladium(0) and pa~kadium(r1).The two
main topics are the reactions of organic
halides and pseudohalides catalyzed by
palladium(o), including examples such as
the Heck reaction and the Suzuki coupling (Section l ) , and the reactions of ally1
compounds, again catalyzed by palladium(o) (Section 2). As an example to illustrate the systematic arrangement of the
subject matter adopted throughout the
book, let us assume that we wish to find
the Stille reaction in Chapter 4. This reaction uses organic halides or pseudohalides
as substrates, so we go first to Section 1. I .
An organometallic compound is used as
the coreactant, which takes us to Section
1.1.4. More specifically this is an organotin compound, so finally we arrive at Section The Stille reaction could ac-
71, VCH Yerlug.s~e.sell.ssrh~/~
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tually be found more easily from the contents list, but the same would not be true
of the related coupling reactions using
organocopper or organozinc compounds,
as these are not named reactions-for these
one must rely on the system described
Chapter 5 (22 pp.) covers other reactions that could not appropriately be included in the preceding chapters, such as
the palladium-catalyzed Cope rearrangement and the decarbonylation of aldehydes.
In his preface the author writes that it is
better to finish an imperfect book than
never to finish a perfect one. In any event
this is a very good and useful book which
provides a detailed survey of palladium
chemistry. There is scarcely a single important publication that is not cited. It
should be followed in due course by an
updated second edition.
Gerald Dyker
FB6, Organische
und Metallorganische Chemie
der Universitat-Gesamthochschule
Duisburg (Germany)
Metals and Ligand Reactivity. By
E. C. Constable. VCH Verlagsgesellschaft, Weinheim, 1996. 308 pp.,
hardcover DM 128.00/paperback DM
What common ground is there between
coordination chemistry, a traditional area
of inorganic chemistry, and organic chemistry? That is the question addressed by
Edwin C. Constable in the new and completely revised edition of the above book;
the reader seeking an answer will find it
here. The author discusses a large number
of examples which show that “inorganic”
coordination compounds can certainly
undergo “organic” reactions. and that
complexation with metal ions alters the
reactivity of “organic” molecules. The
discussion spans the range from special
types of syntheses and aspects of (metal1o)supramolecular chemistry --a modern
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