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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.
List of contents
Catalytic Addition of C?-?H Bonds to C?-?C Multiple Bonds.- Chelation-Assisted Arylation via C-H Bond Cleavage.- Catalytic Arylation and Vinylation Reactions Directed by Anionic Oxygen Functions via Cleavage of C?-?H and C?-?C Bonds.- Chelate-Directed Oxidative Functionalization of Carbon-Hydrogen Bonds: Synthetic Applications and Mechanistic Insights.- Directed C?-?C Bond Activation by Transition Metal Complexes.- Directed Rhodium-Catalyzed Hydroformylation of Alkenes.- Directed Mizoroki-Heck Reactions.
Summary
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.
Additional text
From the reviews:
"This volume provides summaries of transition metal catalyzed reactions where a directed metalation is involved. … Chatani has compiled seven reviews that are written by experts in the field, are heavily referenced, and are amply illustrated. This work also contains a subject index for this volume and an author index for all 24 volumes in the series. Summing Up: Recommended. Graduate students through professionals." (J. Landesberg, CHOICE, Vol. 45 (10), June, 2008)
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From the reviews:
"This volume provides summaries of transition metal catalyzed reactions where a directed metalation is involved. ... Chatani has compiled seven reviews that are written by experts in the field, are heavily referenced, and are amply illustrated. This work also contains a subject index for this volume and an author index for all 24 volumes in the series. Summing Up: Recommended. Graduate students through professionals." (J. Landesberg, CHOICE, Vol. 45 (10), June, 2008)
