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Directed metalation is recognized as one of the most useful
methodologies for the regio- and stereoselective generation of
organometallic species, the generation of which necessarily leads
to the selective formation of organic products. Cyclometalation
using Li, Mn, and Pd, and directed hydrometalation and
carbometalation using Al and Zn, have been utilized for regio-
and/or stereoselective synthesis for decades. Recently, a new
chelation-assisted methodology has been developed not only for
controlling regio- and stereoselectivity of reactions, but also for
accelerating reactions. In particular, chelation-methodology has
been utilized as a new activation method, in which a carbon-metal
bond is generated directly from a C-H bond; a reaction rarely
achieved using conventional methods. A wide variety of catalytic
functionalization reactions of C-H bonds by the utilization of a
chelation, have been developed recently and are comprehensively
discussed in this book by leading experts. In addition, new
approaches to directed hydrometalation and directed carbometalation
as a key step are also discussed. A unique stereo- and
regioselective hydroformylation has been developed through the
utilization of directed hydrometalation. The regioselective
Mizoroki-Heck reaction is another example in which directed
carbometalation can be used to achieve a high regioselectivity.
These examples emphasize how these innovative methodologies are
contributing to different fields of chemistry.
Directed metalation is recognized as one of the most useful
methodologies for the regio- and stereoselective generation of
organometallic species, the generation of which necessarily leads
to the selective formation of organic products. Cyclometalation
using Li, Mn, and Pd, and directed hydrometalation and
carbometalation using Al and Zn, have been utilized for regio-
and/or stereoselective synthesis for decades. Recently, a new
chelation-assisted methodology has been developed not only for
controlling regio- and stereoselectivity of reactions, but also for
accelerating reactions. In particular, chelation-methodology has
been utilized as a new activation method, in which a carbon-metal
bond is generated directly from a C-H bond; a reaction rarely
achieved using conventional methods. A wide variety of catalytic
functionalization reactions of C-H bonds by the utilization of a
chelation, have been developed recently and are comprehensively
discussed in this book by leading experts. In addition, new
approaches to directed hydrometalation and directed carbometalation
as a key step are also discussed. A unique stereo- and
regioselective hydroformylation has been developed through the
utilization of directed hydrometalation. The regioselective
Mizoroki-Heck reaction is another example in which directed
carbometalation can be used to achieve a high regioselectivity.
These examples emphasize how these innovative methodologies are
contributing to different fields of chemistry.
Exploring the importance of Richard F. Heck's carbon coupling
reaction, this book highlights the subject of the 2010 Nobel Prize
in Chemistry for palladium-catalyzed cross couplings in organic
synthesis, and includes a foreword from Nobel Prize winner Richard
F. Heck. The Mizoroki-Heck reaction is a palladium-catalyzed
carbon-carbon bond forming process which is widely used in organic
and organometallic synthesis. It has seen increasing use in the
past decade as chemists look for strategies enabling the controlled
construction of complex carbon skeletons. The Mizoroki-Heck
Reaction is the first dedicated volume on this important reaction,
including topics on:* mechanisms of the Mizoroki-Heck reaction*
intermolecular Mizoroki-Heck reactions* focus on regioselectivity
and product outcome in organic synthesis* waste-minimized
Mizoroki-Heck reactions* intramolecular Mizoroki-Heck reactions*
formation of heterocycles* chelation-controlled Mizoroki-Heck
reactions* the Mizoroki-Heck reaction in domino processes*
oxidative heck-type reactions (Fujiwara-Moritani reactions)*
Mizoroki-Heck reactions with metals other than palladium* ligand
design for intermolecular asymmetric Mizoroki-Heck reactions*
intramolecular enantioselective Mizoroki-Heck reactions*
desymmetrizing Mizoroki-Heck reactions* applications in
combinatorial and solid phase syntheses, and the development of
modern solvent systems and reaction techniques* the asymmetric
intramolecular Mizoroki-Heck reaction in natural product total
synthesis Several chapters are devoted to asymmetric Heck reactions
with particular focus on the construction of otherwise
difficult-to-obtain sterically congested tertiary and quaternary
carbons. Industrial and academic applications are highlighted in
the final section. The Mizoroki-Heck Reaction will find a place on
the bookshelves of any organic or organometallic chemist. "I am
convinced that this book will rapidly become the most important
reference text for research chemists in academia and industry who
seek orientation in the rapidly growing and - for the layman -
confusing field described as the "'Mizoroki-Heck reaction'."
(Synthesis, March 2010)
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