Gold Catalysis

The following sections are included:

• Contents
• CONTRIBUTORS

Gold, “the king of metals”, is a fascinating element that has intimately accompanied the evolution of civilizations. Given its physical and chemical properties, this metal has naturally found a large variety of applications in our current everyday life. However, it is worth mentioning that synthetic organic chemists, who have employed several other less “popular” metals in the development of homogeneously catalyzed transformations, have surprisingly neglected its use up to the end of the last century. Homogeneous gold catalysis has seen an impressive development during the last ten years and has come to be recognized as a powerful synthetic tool. After a short introduction of the gold element (Section 1.1), this chapter presents the seminal studies that have set the foundations for its recent use in synthetic organic chemistry (Section 1.2). The two following sections concern the general reactivity of electrophilic gold species (Section 1.3) and the different classes of catalysts that are currently employed in homogeneous gold catalysis (Section 1.4).

The following sections are included:

• Introduction
• Homogeneous Gold-Catalyzed Oxidation Reactions with External Oxidants
• Homogeneous Gold-Catalyzed Intramolecular Redox Reactions
• Homogeneous Gold-Catalyzed Reductions
• Summary
• Acknowledgment
• References

The following sections are included:

• Introduction
• Addition of Carbon Nucleophiles to Alkynes
• Addition of Carbon Nucleophiles to Allenes
• Addition of Carbon Nucleophiles to Alkenes
• Addition of Carbon Nucleophiles to Carbonyls
• Addition of Carbon Nucleophiles to Iminiums
• Addition of Arenes and Alkenes to Miscellaneous Electrophiles
• Conclusion
• References

The following sections are included:

• Introduction
• Nitrogen Nucleophiles
• Oxygen Nucleophiles
• Sulfur Nucleophiles
• Other Heteroatom Nucleophiles
• Conclusion
• References

The following sections are included:

• Introduction
• Synthesis of Heterocycles via Gold-Catalyzed Heteroatom Addition to Unsaturated C–C Bonds
• Synthesis of Heterocyclic Derivatives through Gold-Catalyzed Cyclization of Polyunsaturated Compounds
• Synthesis of Heterocyclic Compounds via α-Oxo Gold Carbenoid
• Synthesis of Heterocyclic Derivatives through Gold-Catalyzed Cycloaddition Reactions
• Synthesis of Heterocyclic Derivatives through Gold-Catalyzed Activation of Carbonyl Groups and Alcohols
• Synthesis of Heterocyclic Compounds through Gold-Mediated C–H Bond Functionalization
• Gold-Catalyzed Domino Cyclization/Oxidative Coupling Reactions
• Conclusions
• References

The following sections are included:

• Introduction
• Gold-Catalyzed Three-Component Reactions
• Gold-Catalyzed Three-Component Reactions/Tandem Cyclization
• Concluding Remarks
• Acknowledgments
• References

The following sections are included:

• Introduction
• Oxo Alkynes
• Oxodienes
• Iminoalkynes
• Aminoalkynes
• Nitroalkyne
• Alkynyl Nitrone
• Allenyl Acetals
• Epoxyalkynes
• Alkynyl Hydroxylamine
• Conclusion
• References

The following sections are included:

• Introduction
• Gold Complexes
• Gold-Catalyzed Cyclization of 1, n-Enynes
• References

The following sections are included:

• Introduction
• 1,2-O-Acyl Migrations
• 1,3-O-Acyl Migrations
• Conclusion
• References

The following sections are included:

• Introduction
• Dual-Catalytic Gold and Palladium Cross-Coupling Reactions
• Fundamental Understanding through Stoichiometric Experiments
• Challenges
• Outlook
• References

The following sections are included:

• Introduction
• Theoretical Considerations
• Mechanistic Considerations
• Acknowledgment
• References

The field of gold catalysis has experienced exponential expansion within the last 15 years [1]. The majority of gold-catalyzed reactions rely on the activation of carbon–carbon π-bonds enhancing the electrophilicity of the unsaturated moiety and therefore favoring nucleophilic additions to the carbon–carbon bond. Rare examples employing the activation of a nucleophilic derivative have been reported. The enantioselective transformations employing gold catalysts have appeared only recently and rely mainly on gold(I) linear chiral complexes, which make the control of stereogenic centers much more difficult [2]. This situation therefore slowed the expansion of the field and made it difficult to generalize chiral systems. This chapter intends to present the seminal examples related to asymmetric catalysis focusing exclusively on the use of a chiral catalyst [3]…

The following sections are included:

• Introduction
• Addition of Heteroatoms
• Enyne Cyclizations
• Hydroarylation Reactions
• Aldol Reactions
• Conclusion
• References

The following section is included:

• INDEX