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ByOlaf Khl Functionalised N-Heterocyclic Carbene Complexes Wiley 2010 364 pp.

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Book Review
Published online in Wiley Online Library: 26 January 2011
( DOI 10.1002/aoc.1768
Book Review
Functionalised N-Heterocyclic Carbene Complexes
Wiley, 2010, 364 pp.
price £95.00/euro 114.00 (hardback)
ISBN 978-0-470-71215-3
The chemistry of N-heterocyclic
carbenes (NHCs) and their complexes has matured considerably
since Arduengo’s first isolation of a
free NHC. Not only are NHCs nowadays useful organocatalysts in their
own right, but more importantly,
they are commonly used as stateof-the-art ligands for organometallic catalysts. It is thus not surprising that numerous publications on
NHCs appear almost on a daily basis. Several review papers and even
books on various aspects of their
rich chemistry or catalytic applications have also been published in recent years. The question then
arises as to whether a new book can provide any additional value
to the readership. The textbook Functionalised N-Heterocyclic Carbene Complexes attempts to do this by introducing major trends in
the development and applications of functionalized NHC ligands
with the objective of assisting readers in developing and applying
their own functionalized NHCs. There are overall six chapters spanning around 350 pages. Chapter 1 gives a general introduction on
NHCs and their ligand properties and details common synthetic
routes to ligand precursors (imidazolium salts and free carbenes)
and the respective complexes, which is useful for readers unfamiliar with this field. The second chapter discusses the purpose
of functionalization in terms of hemilability, immobilization, chirality and catalytic applications. The subsequent Chapters 3 and
4 deal with functionalization of NHCs with neutral and anionic
groups, respectively, covering nitrogen, oxygen and phosphorus
donors, and to a smaller extent sulfur donors. The remaining two
chapters describing chirality and NHCs derived from natural products – such as caffeine, thiamine and amino acids – seem to be out
of place. Strictly speaking, only carbenes derived from the latter
carry additional functional groups that can add value to the NHC.
Overall, the text is readable, covering a broad range of examples
and useful references to the original literature and resembling
a review paper rather than a chemistry textbook. However, the
overall format and technical quality have to be sharply criticized.
With the good intention of highlighting key findings described in
the main text, the author often uses inserted statements labeled
as ‘Advantage’, ‘Disadvantage’ or simply ‘Note’. In many cases, the
author fulfilled his intention. Unfortunately, in many other cases
these statements are often not well separated from the main
text and seem to appear randomly with irrelevant or sometimes
even incorrect information. One example is the statement that
N-alkylation of azoles is a method ‘limited to primary alkyl halides
as secondary and tertiary alkyl halides are subject to unwanted
elimination reactions’. This statement is only partially true, since
there are many examples of N-alkylation with secondary alkyl
halides. Furthermore, I have to criticize the inadequate and wrong
nomenclature used in this book. All NHC precursors have been
termed imidazolium salts, regardless of whether they are derived
from imidazole, imidazoline (saturated), benzimidazole (benzannulated), triazole or thiazole. Another shortcoming is the poor
quality of the figures, which are limited to clumsily drawn chemical structures and schemes of variable and inconsistent sizes. In
some chemical structures the nitrogen atom of the NHC was even
missing, and in many chemical formulae the number of atoms
was not in subscript. It is also surprising that the book lacks other
figures such as useful diagrams, pictorial representations or tables for the purpose of comparison. Finally, the main text of the
book requires further editing in order to eliminate the numerous
typographical errors.
In conclusion, the reader is advised to reflect for him/herself prior
to purchase whether the admittedly large number of examples on
functionalized NHC complexes described in this book overrides its
poor technical quality.
Han Vinh Huynh
National University of Singapore, Singapore
Appl. Organometal. Chem. 2011, 25, 565
c 2011 John Wiley & Sons, Ltd.
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khl, byolaf, carbene, 2010, functionalised, 364, complexes, heterocyclic, wiley
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