Palladium Reagents and Catalysts

New Perspectives for the 21st Century
1. Auflage 2004
ISBN: 978-0-470-85032-9
Verlag: Wiley

Buch, Englisch, 670 Seiten, Format (B × H): 172 mm x 250 mm, Gewicht: 1275 g

Jiro Tsuji, one of the pioneers in this field of organic synthesis, provides synthetic organic chemists with a remarkable overview of the many applications of organopalladium chemistry. Tsuji discusses the recent developments in the field as well as the explosive growth over the last five years.
Highlighting the most recent discoveries in this rapidly expanding field, the book;
- Focuses on new aspects of organopalladium chemistry, putting emphasis on synthetic applications
- Investigates the new perspectives on the synthetic uses of contemporary organopalladium chemistry

This volume, together with Innovations in Organic Synthesis, Tsuji's previous title, provides complete coverage of over 40 years of organopalladium chemistry.

Palladium Reagents and Catalysts: New Perspectives for the 21st Century is an essential reference source and companion for students, and both industrial and academic research chemists working in organic synthesis, particularly on synthesis of natural products and medicinal compounds.

Those studying development of new synthetic methodology and organometallic chemistry will also find this book valuable.

Autoren/Hrsg.

Tsuji, Jiro

Fachgebiete

• Naturwissenschaften Chemie Chemie Allgemein Pharmazeutische Chemie, Medizinische Chemie
• Naturwissenschaften Chemie Chemie Allgemein Chemometrik, Chemoinformatik
• Naturwissenschaften Chemie Chemie Allgemein Toxikologie, Gefahrstoffe, Sicherheit in der Chemie
• Naturwissenschaften Chemie Chemie Allgemein Chemische Labormethoden, Stöchiometrie

Inhaltsverzeichnis

Preface.
Abbreviations.

1 The Basic Chemistry of Organopalladium Compounds.

1.1 Characteristic Features of Pd-Promoted or –Catalyzed Reactions.

1.2 Palladium Compounds, Complexes, and Ligands Widely Used in Organic Synthesis.

1.3 Fundamental Reactions of Pd Compounds.

1.3.1 ‘Oxidative’ Addition.

1.3.2 Insertion.

1.3.3 Transmetallation.

1.3.4 Reductive Elimination.

1.3.5 ß-H Elimination (ß-Elimination, Dehydropalladation).

1.3.6 Elimination of ß-Heteroatom Groups and ß-Carbon.

1.3.7 Electrophilic Attack by Organopalladium Species.

1.3.8 Termination of Pd-Catalyzed or –Promoted Reactions and a Catalytic Cycle.

1.3.9 Reactions Involving Pd(II) Compounds and Pd(0) Complexes.

References.

2 Oxidative Reactions with Pd(II) Compounds.

2.1 Introduction.

2.2 Reactions of Alkenes.

2.2.1 Introducti on.

2.2.2 Reaction with Water.

2.2.3 Reactions with Alcohols and Phenols.

2.2.4 Reactions with Carboxylic Acids.

2.2.5 Reactions with Amines.

2.2.6 Reactions with Carbon Nucleophiles.

2.2.7 Oxidative Carbonylation.

2.2.8 Reactions with Aromatic Compounds.

2.2.9 Coupling of Alkenes with Organometallic Compounds.

2.3 Stoichiometric Reactions of p-Allyl Complexes.

2.4 Reactions of Conjugated Dienes.

2.5 Reactions of Allenes.

2.6 Reaction of Alkynes.

2.7 Homocoupling and Oxidative Substitution Reactions of Aromatic Compounds.

2.8 Regioselective Reactions Based on Chelation and Participation of Heteroatoms.

2.9 Oxidative Carbonylation of Alcohols and Amines.

2.10 Oxidation of Alcohols.

2.11 Enone Formation from Ketones and Cycloalkenylation.

References.

3 Pd(0)-Catalyzed Reactions of sp2Organic Halides and Pseudohalides.

3.1 Introduction.

3.2 Reactions with Alkenes (Mizoroki–Heck Reaction).

3.2.1 Introduction.

3.2.2 Catalysts and Ligands.

3.2.3 Reaction Conditions (Bases, Solvents, and Additives).

3.2.4 Halides and Pseudohalides.

3.2.5 Alkenes.

3.2.6 Formation of Neopentylpalladium and its Termination by Anion Capture.

3.2.7 Intramolecular Reactions.

3.2.8. Asymmetric Reactions.

3.2.9 Reactions with 1,2-, 1,3-, and 1,4-Dienes.

3.2.10 Amino Heck Reactions of Oximes.

References.

3.3 Reactions of Aromatics and Heteroaromatics.

3.3.1 Arylation of Heterocycles.

3.3.2 Intermolecular Arylation of Phenols.

3.3.3 Intermolecular Polyarylation of Ketones.

3.3.4 Intramolecular Arylation of Aromatics.

References.

3.4 Reactions with Alkynes.

3.4.1 Introduction.

3.4.2 Reactions of Terminal Alkynes to Form Aryl- and Alkenylalkynes (Sonogashira Coupling).

References.

3.4.3 Reactions of Internal and Terminal Alkynes with Aryl and Alkenyl Halides via Insertion.

References.

3.5 Carbonylation and Reactions of Acyl Chlorides.

3.5.1 Introduction.

3.5.2 Formation of Carboxylic Acids, Esters, and Amides.

3.5.3 Formation of Aldehydes and Ketones.

3.5.4 Reactions of Acyl Halides and Related Compounds.

3.5.5 Miscellaneous Reactions.

References.

3.6 Cross-Coupling Reactions with Organometallic Compounds of the Main Group Metals via Transmetallation.

3.6.1 Introduction.

3.6.2 Organoboron Compounds (Suzuki–Miyaura Coupling).

References.

3.6.3 Organostannanes (Kosugi–Migita–Stille Coupling).

3.6.4 Organozinc Compounds (Negishi Coupling).

3.6.5 Organomagnesium Compounds.

3.6.6 Organosilicon Compounds (Hiyama Coupling).

References.

3.7 Arylation and Alkenylation of C, N, O, S, and P Nucleophiles.

3.7.1 a-Arylation and a-Alkenylation of Carbon Nucleophiles.

3.7.2 Intramolecular Attack of Aryl Halides on Carbonyl Groups.

Reference

Über Autor(innen)

Jiro Tsuji is the author of Palladium Reagents and Catalysts: New Perspectives for the 21st Century, published by Wiley.