Metal Catalyzed Cascade Reactions

Transition metal-catalyzed cascade reactions are an elegant approach to complex molecular scaffolds. Besides their esthetics and increase in structural complexity, they have also become mechanistic challenges for the combination of organometallic elementary steps. As a consequence, cascade reactions have revolutionized synthetic strategies and conceptual thinking. The authors highlight cyclization via carbopalladation and acylpalladation and Heck-pericyclic sequences. They discuss p-allyl palladium-based cascade reactions, Michael-type additions as an entry to transition-metal-promoted cyclizative transformations, and sequential or consecutive palladium-catalyzed processes, and show Pauson-Khand cascades, metal-catalyzed cyclizations of acyclic precursors, as well as cascade and sequential ruthenium-catalyzed transformations. Therefore, the reader finds overview of an exciting and highly dynamic field of a new and innovative methodological concept.

List of contents

Ei-Ichi Negishi, Guangwei Wang, and Gangguo Zhu: Palladium-Catalyzed Cyclization via Carbopalladation and Acylpalladation.- Paultheo von Zezschwitz, and Armin De Meijere: Domino Heck-Pericyclic Reactions.- Nitin T. Patil, and Yoshinori Yamamoto: Palladium Catalyzed Cascade Reactions Involving p-Allyl Palladium Chemistry.- Geneviève Balme, Didier Bouyssi, and Nuno Monteiro: The Virtue of Michael-Type Addition Processes in the Design of Transition Metal-Promoted Cyclizative Cascade Reactions.- Thomas J. J. Müller: Sequentially Palladium Catalyzed Processes.- Javier Pérez-Castells: Cascade Reactions Involving Pauson-Khand and Related Processes.- Corinne Aubert, Louis Fensterbank, Vincent Gandon, and Max Malacria: Complex Polycyclic Molecules from Acyclic Precursors via Transition Metal-Catalyzed Cascade Reactions.- Christian Bruneau, Sylvie Dérien, and Pierre H. Dixneuf: Cascade and Sequential Catalytic Transformations initiated by Ruthenium Catalysts.

Summary

Transition metal-catalyzed cascade reactions are an elegant approach to complex molecular scaffolds. Besides their esthetics and increase in structural complexity, they have also become mechanistic challenges for the combination of organometallic elementary steps. As a consequence, cascade reactions have revolutionized synthetic strategies and conceptual thinking. The authors highlight cyclization via carbopalladation and acylpalladation and Heck-pericyclic sequences. They discuss p-allyl palladium-based cascade reactions, Michael-type additions as an entry to transition-metal-promoted cyclizative transformations, and sequential or consecutive palladium-catalyzed processes, and show Pauson-Khand cascades, metal-catalyzed cyclizations of acyclic precursors, as well as cascade and sequential ruthenium-catalyzed transformations. Therefore, the reader finds overview of an exciting and highly dynamic field of a new and innovative methodological concept.

Additional text

From the reviews:

"This volume, the latest in the Topics in Organometallic Chemistry series, features reports from eight research groups active in cascade catalysis. It does not focus on particular reactions or periodic groups but rather offers a broad overview of methods to generate multiple bonds in a given organic molecule with stereo- and regiocontrol. Its mechanistic focus complements a recent review of cascade reactions in the context of total synthesis... this book offers several new reactions and approaches to complex molecular synthesis for those considering cascade or domino reactions. Despite several minor quibbles, it effectively accomplishes the goal of compiling several complementary reviews on this burgeoning field. The complexity and number of metal-mediated elementary steps renders this book best suited to the student of synthesis already familiar with organometallic chemistry." (Michael A. Tarselli and Michel R. Gagné, Journal of the American Chemical Society, Vol. 129 (7), 2007)
"Cascade reactions, also known as domino reactions, are multibond-forming processes in which the first reaction creates the functionality/geometry necessary for the second reaction to proceed, and so on. Volume 19 of the Topics in Organometallic Chemistry series comprises eight chapters written by experts in the relevant areas and is heavily weighted towards palladium(0)-catalysed processes (5 chapters). Additionally, there is an excellent chapter on the Pauson-Khand reaction (mainly cobald catalysis) and on metathesis (ruthenium)… . Overall, this would not be considered a volume for personal libraries, but is well worth consulting when appropriate. It is to be recommended on that basis." (Ron Grigg, Platinum Metals Review, Vol. 52 (2), 2007)
"This is volume 19 of the publishers’ series Topics in Organometallic Chemistry. … The volume represents essential reading for researchers, teachers and students, both experts andnovices seeking to be introduced to an exciting field of innovative methodology. It deserves to be widely read and debated … . I will certainly want it on my shelves and I have no doubt but that this wish will be shared by all academic and industrial researchers in organometallics, organic chemistry, inorganic chemistry, pharmaceutical and medicinal chemistry." (Current Engineering Practice, 2007)

Report

From the reviews:

"This volume, the latest in the Topics in Organometallic Chemistry series, features reports from eight research groups active in cascade catalysis. It does not focus on particular reactions or periodic groups but rather offers a broad overview of methods to generate multiple bonds in a given organic molecule with stereo- and regiocontrol. Its mechanistic focus complements a recent review of cascade reactions in the context of total synthesis... this book offers several new reactions and approaches to complex molecular synthesis for those considering cascade or domino reactions. Despite several minor quibbles, it effectively accomplishes the goal of compiling several complementary reviews on this burgeoning field. The complexity and number of metal-mediated elementary steps renders this book best suited to the student of synthesis already familiar with organometallic chemistry." (Michael A. Tarselli and Michel R. Gagné, Journal of the American Chemical Society, Vol. 129 (7), 2007)
"Cascade reactions, also known as domino reactions, are multibond-forming processes in which the first reaction creates the functionality/geometry necessary for the second reaction to proceed, and so on. Volume 19 of the Topics in Organometallic Chemistry series comprises eight chapters written by experts in the relevant areas and is heavily weighted towards palladium(0)-catalysed processes (5 chapters). Additionally, there is an excellent chapter on the Pauson-Khand reaction (mainly cobald catalysis) and on metathesis (ruthenium)... . Overall, this would not be considered a volume for personal libraries, but is well worth consulting when appropriate. It is to be recommended on that basis." (Ron Grigg, Platinum Metals Review, Vol. 52 (2), 2007)
"This is volume 19 of the publishers' series Topics in Organometallic Chemistry. ... The volume represents essential reading for researchers, teachers and students, both experts andnovices seeking to be introduced to an exciting field of innovative methodology. It deserves to be widely read and debated ... . I will certainly want it on my shelves and I have no doubt but that this wish will be shared by all academic and industrial researchers in organometallics, organic chemistry, inorganic chemistry, pharmaceutical and medicinal chemistry." (Current Engineering Practice, 2007)

Product details

• Assisted by: Thoma J J Müller (Editor), Thomas J J Müller (Editor), Thomas J. J. Müller (Editor), Thomas J.J. Müller (Editor)
• Publisher: Springer, Berlin
• Languages: English
• Product format: Paperback / Softback
• Released: 06.10.2010
• EAN: 9783642069505
• ISBN: 978-3-642-06950-5
• No. of pages: 340
• Dimensions: 155 mm x 19 mm x 235 mm
• Weight: 534 g
• Illustrations: X, 340 p.
• Series: Topics in Organometallic Chemistry; Topics in Organometallic Chemistry
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Anorganische Chemie, C, ORGANOMETALLIC CHEMISTRY, Katalyse, Catalysis, Chemistry and Materials Science, Inorganic Chemistry, transition metal