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The Mizoroki-Heck Reaction

Author: Martin Oestreich; Wiley InterScience (Online service)
Publisher: Hoboken, NJ : John Wiley & Sons, ©2009.
Edition/Format:   eBook : Document : EnglishView all editions and formats
Summary:

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  Read more...

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Genre/Form: Electronic books
Electronic resource
Material Type: Document, Internet resource
Document Type: Internet Resource, Computer File
All Authors / Contributors: Martin Oestreich; Wiley InterScience (Online service)
ISBN: 9780470716076 047071607X
OCLC Number: 352829723
Description: 1 online resource (600)
Contents: Cover --
Contents --
Foreword --
Preface --
Contributors --
1 Mechanisms of the Mizoroki8211;Heck Reaction --
1.1 Introduction --
1.2 Mechanism of the Mizoroki8211;Heck Reaction when the Catalytic Precursor is Pd(OAc)2 in the Absence of Ligand --
1.3 Mechanism of the Mizoroki8211;Heck Reaction when the Catalytic Precursor is Pd(OAc)2 Associated with Monophosphine Ligands --
1.3.1 Pd(0) Formation from Pd(OAc)2 in the Presence of a Monophosphine Ligand --
1.3.2 Oxidative Addition --
1.3.3 Complexation/Insertion of the Alkene --
1.3.4 Multiple Role of the Base --
1.3.5 Catalytic Cycle --
1.4 Mechanism of the Mizoroki8211;Heck Reaction when the Catalytic Precursor is Pd(OAc)2 Associated with Bisphosphine Ligands --
1.4.1 Pd(0) Formation from Precursor --
1.4.2 Oxidative Addition --
1.4.3 Complexation/Insertion of the Alkene Regioselectivity --
1.4.4 Catalytic Cycles --
1.5 Mechanism of the Mizoroki8211;Heck Reaction when the Catalytic Precursor is a P, C-Palladacycle --
1.5.1 Pd(0) Formation from a P, C-Palladacycle --
1.5.2 Catalytic Cycle --
1.6 Mechanism of the Mizoroki8211;Heck Reaction when the Ligand is an N-Heterocyclic Carbene --
1.6.1 Oxidative Addition --
1.6.2 Complexation/Insertion of the Alkene --
1.6.3 Catalytic Cycles --
1.7 Mechanism of the Mizoroki8211;Heck Reaction when the Ligand is a Bulky and Electron-Rich Monophosphine --
1.7.1 Oxidative Addition --
1.7.2 Complexation/Insertion of the Alkene --
1.7.3 Role of the Base in the Recycling of the Pd(0) Complex --
1.7.4 Catalytic Cycle --
1.8 Conclusion --
References --
2 Focus on Catalyst Development and Ligand Design --
2.1 Introduction --
2.2 General Considerations: Types of Catalytic System --
2.2.1 Substrate Dependence --
2.2.2 Ancillary Ligands --
2.2.3 Bases --
2.2.4 Additives --
2.2.5 Media --
2.2.6 Temperature --
2.3 Four Types of Intermolecular Mizoroki8211;Heck Catalytic System --
2.3.1 The Type 1 Catalytic System --
2.3.2 The Type 2 Catalytic System --
2.3.3 The Type 3 Catalytic System --
2.3.4 The Type 4 Catalytic System --
2.4 Palladium Precatalysts in Type 1 and Type 2 Mizoroki8211;Heck Reactions --
2.4.1 SRPCs --
2.4.2 Nanoparticles --
2.4.3 Supported Catalysts: Leaching versus Recycling --
2.4.4 Carbene Complexes --
2.4.5 Palladacycles --
2.4.6 Nonphosphine Complexes --
References --
3 Focus on Regioselectivity and Product Outcome in Organic Synthesis --
3.1 Introduction --
3.2 Mechanistic Aspects --
3.2.1 Oxidative Addition --
3.2.2 8226; -Complex Formation and Migratory Insertion --
3.2.3 8226; -H-Elimination and Palladium(0) Recycling --
3.2.4 Cyclic Alkenes and Double-Bond Migration --
3.2.5 Aryl Scrambling --
3.2.6 Mizoroki8211;Heck Reactions with Vinyl8211;X Substrates --
3.2.7 Reactions Using Low Palladium Catalyst Concentration --
3.2.8 Carbonylative, Decarbonylative and Desulfitative Mizoroki8211;Heck Reactions --
3.3 Electron-Rich Alkenes --
3.3.1 Internal Arylations --
3.3.2 Terminal Arylations --
3.3.3 Vinylations --
3.4 Allylic Alkenes --
3.4.1 Terminal Couplings --
3.4.2 Internal Couplings --
3.5 Electron-Poor Alkenes --
3.5.1 Arylations and Double Arylations --
3.5.2 Examples from Pharmaceutical and Medicinal Chemistry --
References --
3.6 Summary --
4 Waste-Minimized Mizoroki8211;Heck Reactions --
4.1 Introduction --
4.2 Oxidative Coupling of Arenes.
Responsibility: editors, Martin Oestreich.

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