Metal-Catalyzed Cross-Coupling Reactions

by de Meijere, Armin; Diederich, François

• ISBN13: 9783527305186
• ISBN10: 3527305181
• Edition: 2nd
• Format: Hardcover
• Copyright: 2004-10-15
• Publisher: Wiley-VCH

Summary

In this second, completely revised and enlarged edition, Francois Diederich is joined by Armin de Meijere in bringing together in two comprehensive volumes everything of importance related to C-C and C-N cross-coupling reactions. The range of applications covered extends from the synthesis of complex natural materials via supramolecular chemistry right up to materials science. Internationally renowned experts pass on to the reader the current level of knowledge, while critical analyses of the latest developments and applications allow users to quickly decide for themselves on which strategies are available for solving their synthesis problems. In particular the experimental guidelines for key reactions developed by the authors for the widest possible range of applications testify to the practical advantages this handbook offers every organic chemist.

Author Biography

Armin de Meijere studied chemistry at the universities of Freiburg and G÷ttingen and obtained his doctorate at the latter. Following postdoctoral training under Kenneth B. Wiberg at Yale University in New Haven, USA, he returned to G÷ttingen in 1971 to gain his lectureship qualification. He became Professor of Organic Chemistry at the University of Hamburg in 1977, and took up the same chair at the University of G÷ttingen in 1989, where he is currently the Dean of the Faculty of Chemistry.<br> Armin de Meijere has been visiting professor at universities in the USA, Israel, Italy, France, as well as at the Indian Institute of Science in Bangalore. He was elected a member of the Norwegian Academy of Sciences and Letters in 1992, and in 1996 received the Alexander von Humboldt-Gay Lussac Prize of the French Ministry for Higher Education and Research. In 1997 he was elected member of the Braunschweigische Wissenschaftliche Gesellschaft, and as an Honorary Professor of the St. Petersburg State University, Russia.<br> He is editor or member of the Editorial Board for a number of scientific journals, periodicals and books, while his own achievements have been published in over 520 publications. <br> <br> Frantois Diederich was born in 1952 in Luxembourg. He received his doctorate in 1979 from the University of Heidelberg and subsequently pursued postdoctoral studies at the University of California at Los Angeles (UCLA). After his postdoctoral qualification at the Max-Planck-Institut fnr medizinische Forschung, he joined the Department of Chemistry and Biochemistry at UCLA in 1985 where he became a full professor four years later. In 1992, he moved to the ETH Zurich as a member of the Department of Chemistry and Applied Biosciences. Professor Diederich's research interests, documented in more than 420 publications, range from medicinal chemistry with a focus on molecular recognition studies, to advanced fullerene and acetylene-based materials with novel optoelectronic properties. <br> <br>

Table of Contents

Preface.

List of Contributors.

Mechanistic Aspects of Metal-Catalyzed C,C- and C,X-Bond-Forming Reactions

Mechanisms of Cross-Coupling Reactions.

Formation of C,C-Bonds in the Palladium-Catalyzed ¿-Arylation of Carbonyl Compounds and Nitriles.

Key Intermediates in the Formation of C-X (X = N, O, S) bonds in Metal-Catalyzed Reactions 25

Reductive Elimination of C-N, C-O, and C-S Bonds From Organopalladium(II) Complexes.

Summary and Outlook.

Abbreviations.

References.

Metal-Catalyzed Cross-Coupling Reactions of Organoboron Compounds with Organic Halides

Introduction.

Advances in the Synthesis of Organoboron Compounds.

Reaction Mechanism.

Reaction Conditions.

Side Reactions.

Reactions of B-Alkyl Compounds.

Reactions of B-Alkenyl Compounds.

Reactions of B-Aryl Compounds.

Reactions of B-Allyl and B-Alkynyl Compounds.

Reactions Giving Ketones.

Dimerization of Arylboronic Acids.

N-, O-, and S-Arylation.

Abbreviations.

References.

Organotin Reagents in Cross-Coupling Reactions

Introduction.

Mechanism and Methodology.

Natural Product Synthesis.

Organic Synthesis.

Polymer Chemistry.

Inorganic Synthesis.

Conclusions.

Experimental Procedures.

Abbreviations.

References.

Organosilicon Compounds in Cross-Coupling ReactionsScott E. Denmark

Introduction.

Modern Organosilicon-Cross-Coupling.

Mechanistic Studies in Silicon-Cross-Coupling.

Applications to Total Synthesis.

Summary and Outlook.

Experimental Procedures.

Abbreviations.

References.

Cross-Coupling of Organyl Halides with Alkenes: The Heck Reaction

Introduction.

Principles.

Cascade Reactions and Multiple Couplings.

Related Palladium-Catalyzed Reactions.

Enantioselective Heck-Type Reactions.

Syntheses of Heterocycles, Natural Products and Other Biologically Active Compounds Applying Heck Reactions.

Carbopalladation Reactions in Solid-Phase Syntheses.

The Heck Reaction in Fine Chemicals Syntheses.

Conclusions.

Experimental Procedures.

Acknowledgments.

Abbreviations and Acronyms.

References.

Cross-Coupling Reactions to sp Carbon Atoms

Introduction.

Alkynylcopper Reagents.

Alkynyltin Reagents.

Alkynylzinc Reagents.

Alkynylboron Reagents.

Alkynylsilicon Reagents.

Alkynylmagnesium Reagents.

Other Alkynylmetals.

Concluding Remarks.

Experimental Procedures.

Acknowledgments.

Abbreviations and Acronyms.

References.

Carbometallation Reactions

Introduction.

Carbometallation Reactions of Alkynes.

Carbometallation Reactions of Alkenes.

Zinc-Enolate Carbometallation Reactions.

Carbometallation Reactions of Dienes and Enynes.

Carbometallation Reactions of Allenes.

Conclusions.

Experimental Procedures.

Acknowledgments.

References.

Palladium-Catalyzed 1,4-Additions to Conjugated Dienes

Introduction.

Palladium(0)-Catalyzed Reactions.

Palladium(II)-Catalyzed Reactions.

References.

Cross-Coupling Reactions via ¿-Allylmetal In

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