The Mizoroki-Heck Reaction
1. Auflage Februar 2009
608 Seiten, Hardcover
Fachbuch
Kurzbeschreibung
The Heck reaction has experienced ever-increasing importance in several areas of organometallic and organic chemistry. The first dedicated volume on this pivotal reaction, The Heck Reaction provides a comprehensive summary of Heck chemistry, including: current mechanistic understanding; catalyst development and ligand design; inter- and intramolecular Heck reactions; and regio-, diastereo-, and enantioselective variants. Readers will discover details on how to create carbon-carbon bonds and complex carbon skeletons in a highly controlled way, making this a key resource for organic chemists and advanced undergraduate and postgraduate organic chemistry students.
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.
1 Mechanisms of the Mizoroki-Heck Reaction
Anny Jutand
2 Focus on Catalyst Development and Ligand Design
Irina P. Beletskaya and Andrei V. Cheprakov
3 Focus on Regioselectivity and Product Outcome in Organic Synthesis
Peter Nilsson, Kristofer Olofsson and Mats Larhed
4 Waste-Minimized Mizoroki-Heck Reactions
Lukas Gooßen and Käthe Gooßen
5 Formation of Carbocycles
Axel B. Machotta and Martin Oestreich
6 Formation of Heterocycles
Thierry Muller and Stefan Bräse
7 Chelation-Controlled Mizoroki-Heck Reactions
Kenichiro Itami and Jun-ichi Yoshida
8 The Mizoroki-Heck Reaction in Domino Processes
Lutz F. Tietze and Laura M. Levy
9 Oxidative Heck-Type Reactions (Fujiwara-Moritani Reactions)
Eric M. Ferreira, Haiming Zhang and Brian M. Stoltz
10 Mizoroki-Heck Reactions with Metals Other than Palladium
Lutz Ackermann and Robert Born
11 Ligand Design for Intermolecular Asymmetric Mizoroki-Heck Reactions
Anthony G. Coyne, Martin O. Fitzpatrick and Patrick J. Guiry
12 Intramolecular Enantioselective Mizoroki-Heck Reactions
James T. Link and Carol K. Wada
13 Desymmetrizing Heck Reactions
Masakatsu Shibasaki and Takashi Ohshima
14 Combinatorial and Solid-Phase Syntheses
Thierry Muller and Stefan Bräse
15 Mizoroki-Heck Reactions: Modern Solvent Systems and Reaction Techniques
Werner Bonrath, Ulla L´etinois, Thomas Netscher and Jan Schütz
16 The Asymmetric Intramolecular Mizoroki-Heck Reaction in Natural Product Total Synthesis
Amy B. Dounay and Larry E. Overman
