Modern Gold Catalyzed Synthesis

With its impressive features, gold has led to completely new reaction types in recent years, which in turn have strongly influenced both organic catalysis and material science. Other fields where a significant amount of new results has been obtained include nanotechnology, self assembly/supramolecular systems and biochemical/medicinal chemistry. As a result, gold is one of the hottest topics in catalysis at the moment, with an increasing amount of research being carried out in this field. While focusing on homogeneous catalysis, this monograph also covers the main applications in heterogeneous catalysis. Following a look at the gold-catalyzed addition of heteroatom nucleophiles to alkynes, it goes on to discuss gold-catalyzed additions to allenes and alkenes, gold-catalyzed benzannulations, cycloisomerization and rearrangement reactions, as well as oxidation and reduction reactions. The whole is finished off with a section on gold-catalyzed aldol and related reactions and the application of gold-catalyzed reactions to natural product synthesis. Of interest to synthetic chemists and inorganic chemists, as well as organic chemists working in homogeneous catalysis, physical and technical chemists.

ISBN 3527319522   Pages 418 ISBN13 9783527319527 (What's this?)   Weight (grammes) 944 Publisher Wiley-VCH Verlag GmbH   Published in Weinheim Imprint Wiley-VCH Verlag GmbH   Height (mm) 244 Format Hardback   Width (mm) 176 Publication date 18 Apr 2012   Spine width (mm) 23 DEWEY 547.215   Academic level Professional / Scholarly DEWEY edition DC22

HYDROCHLORINATION OF ACETYLENE CATALYZED BY GOLD Introduction Reactions of Alkynes Using Gold Chloride as Catalyst The Correlation of E88 with the Activity of Gold for the Hydrochlorination of Acetylene Central Role of Au3 p and Regeneration of Au/C Catalysts Reaction Mechanism of Alkynes Over Au/C Catalysts Chemical Origin of the E8 Correlation and General Remarks Commercial Processes and Economic Aspects of Vinyl Chloride Monomer Manufacture GOLD-CATALYZED REDUCTION REACTIONS Introduction Hydrogenation of Multiple C C Bonds. Role of the Gold Oxidation State Hydrogenation of a,b-Unsaturated Aldehydes Hydrogenation of Substituted Nitroaromatic Compounds GOLD-CATALYZED BENZANNULATIONS: ASAO - YAMAMOTO BENZOPYRYLIUM PATHWAY Introduction Acetylenic Compounds as 2p Systems Enols as 2p Systems Enol Ethers as 2p Systems Benzynes as 2p Systems Synthesis of Phthalazine Derivatives Application to the Synthesis of Angucyclinone Antibiotics and Other Applications in Total Synthesis Copper-Catalyzed Benzannulations Conclusion GOLD-CATALYZED REACTIONS OF PROPARGYL ESTERS, PROPARGYL ALCOHOLS, AND RELATED COMPOUNDS Introduction and Extent of This Chapter Propargyl Esters Propargyl Ethers Propargyl Alcohols Propargyl Amines Propargyl Carbonates, Amides, and Carbamates Other Propargyl Substitution Patterns Conclusion INTRAMOLECULAR HYDROARYLATION OF ALKYNES Introduction Intramolecular Reactions of Arenes with Alkynes Intramolecular Reactions of Electron-Rich Heteroarenes with Alkynes Conclusion and Outlook GOLD - ALKYNE COMPLEXES Introduction Description of the M - p-Bond Interaction in Alkene and Alkyne Complexes Gold(0) Complexes Gold(I) Complexes Gold(III) complexes Theoretical Studies GOLD - ALKENE COMPLEXES Introduction Gold(0) Derivatives Gold(I) Complexes Gold(III) Complexes Theoretical Studies HYDRATION AND HYDROALKOXYLATION OF CC MULTIPLE BONDS Historical Perspective Gold Catalysts Hydration and Hydroalkoxylation of CC Triple Bonds (Alkynes) Hydration and Hydroalkoxylation of CC Double Bonds (Allenes and Alkenes) GOLD-CATALYZED ALDOL AND RELATED REACTIONS The Gold-Catalyzed Aldol Reaction Related Reactions GOLD-CATALYZED OXIDATION REACTIONS: OXIDATION OF ALKENES Introduction Epoxidation Reactions Aziridination Reactions Oxidative Cleavage of C C Double Bonds Oxygen Transfer to Carbenoids GOLD-CATALYZED OXYGEN-ATOM TRANSFER TO ALKYNES Introduction Oxygen-Atom Transfer from NO Groups Oxygen-Atom Transfer from Sulfoxides Oxygen-Atom Transfer from Epoxides Gold-Catalyzed Oxidative Coupling GOLD-CATALYZED ADDITIONS TO ALKENES: N-NUCLEOPHILES GOLD-CATALYZED ADDITIONS TO ALKENES: O-NUCLEOPHILES OXIDATION OF ALCOHOLS AND CARBOHYDRATES Introduction Selective Oxidation of Alcohols Selective Oxidation of Carbohydrates Future Applications Conclusion APPLICATIONS OF GOLD-CATALYZED REACTIONS TO NATURAL PRODUCT SYNTHESIS Introduction Addition of Heteroatom Nucleophiles to Alkynes Addition of Heteroatom Nucleophiles to Allenes Cycloadditions via Pyrylium Intermediates from o-Alkynylacylarenes Rearrangements of Propargyl Esters Skeletal Rearrangement of 3-Butynyl-N-Oxides: (-)-Cermizine and (?)-Lentiginosine Enyne Cyclizations Propargyl Claisen Rearrangement: Azadirachtin Gold-Catalyzed C?H Activation: (-)-Pterocarpan and Crassifolone Gold-Catalyzed Allylic Amination: (-)-Angustureine Catalytic Asymmetric Aldol Reaction of Isocyanoacetates and Aldehydes GOLD-CATALYZED ADDITION REACTIONS TO ALLENES Introduction Addition of Heteroatom Nucleophiles Addition of Carbon Nucleophiles Conclusion

"In conclusion, this well-written book is recommended to both synthetic chemists and those involved in the study of catalysis." ( Organic Process Research & Development , 1 May 2013)

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