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The Mizoroki-Heck Reaction

ISBN: 978-0-470-03394-4
608 pages
March 2009
The Mizoroki-Heck Reaction (0470033940) cover image
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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Foreword by Professor Richard F. Heck

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

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Martin Oestreich (born in 1971 in Pforzheim/Germany) is currently Professor of Organic Chemistry at the Technische Universität Berlin. He received his diploma degree with Paul Knochel (Marburg, 1996) and his doctoral degree with Dieter Hoppe (Münster, 1999). After a two-year postdoctoral stint with Larry E. Overman (Irvine, 1999-2001), he completed his habilitation with Reinhard Brückner (Freiburg, 2001-2005) and was appointed as Professor of Organic Chemistry at the Westfälische Wilhelms-Universität Münster (2006-2011). He also held visiting positions at Cardiff University in Wales (2005) and at The Australian National University in Canberra (2010).

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"It is by far the most authoritative book in this area written to date and has employed many of the major contributors in the area over recent years to provide chapters, resulting in good...coverage of the literature." (Applied Organimetallic Chemistry , March 2010)

“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)

"This book is a welcome addition to the subject and provides almost all the areas you would want to be covered." (Organic Process Research & Development Journal, 2010)

"The selection and clear arrangement of the competently written chapters of this book is well done, giving a rapid general overview of current knowledge about various aspects of this important reaction." (Angewandte Chemie December 2009)

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