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With its impressive features, gold has led to completely new reaction types in recent years, which in turn have strongly influenced bothorganic 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 atthe 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. Followinga look at the gold-catalyzed addition of heteroatom nucleophiles to alkynes, it goes on to discuss gold-catalyzed additions to allenes andalkenes, 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 naturalproduct synthesis.Of interest to synthetic chemists and inorganic chemists, as well as organic chemists working in homogeneous catalysis, physical andtechnical chemists.
List of contents
HYDROCHLORINATION OF ACETYLENE CATALYZED BY GOLDIntroductionReactions of Alkynes Using Gold Chloride as CatalystThe Correlation of E88 with the Activity of Gold for the Hydrochlorination of AcetyleneCentral Role of Au3 p and Regeneration of Au/C CatalystsReaction Mechanism of Alkynes Over Au/C CatalystsChemical Origin of the E8 Correlation and General RemarksCommercial Processes and Economic Aspects of Vinyl Chloride Monomer ManufactureGOLD-CATALYZED REDUCTION REACTIONSIntroductionHydrogenation of Multiple C¼C Bonds. Role of the Gold Oxidation State Hydrogenation of a,b-Unsaturated AldehydesHydrogenation of Substituted Nitroaromatic Compounds GOLD-CATALYZED BENZANNULATIONS: ASAO - YAMAMOTO BENZOPYRYLIUM PATHWAY Introduction Acetylenic Compounds as 2p Systems Enols as 2p SystemsEnol Ethers as 2p SystemsBenzynes 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 ChapterPropargyl EstersPropargyl 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 COMPLEXESIntroduction 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 ALKENESIntroductionEpoxidation Reactions Aziridination Reactions Oxidative Cleavage of C¼C Double Bonds Oxygen Transfer to Carbenoids GOLD-CATALYZED OXYGEN-ATOM TRANSFER TO ALKYNES Introduction Oxygen-Atom Transfer from NO GroupsOxygen-Atom Transfer from Sulfoxides Oxygen-Atom Transfer from Epoxides Gold-Catalyzed Oxidative Coupling GOLD-CATALYZED ADDITIONS TO ALKENES: N-NUCLEOPHILESGOLD-CATALYZED ADDITIONS TO ALKENES: O-NUCLEOPHILES OXIDATION OF ALCOHOLS AND CARBOHYDRATESIntroductionSelective Oxidation of AlcoholsSelective Oxidation of Carbohydrates Future Applications Conclusion APPLICATIONS OF GOLD-CATALYZED REACTIONS TO NATURAL PRODUCT SYNTHESISIntroduction Addition of Heteroatom Nucleophiles to AlkynesAddition of Heteroatom Nucleophiles to Allenes Cycloadditions via Pyrylium Intermediates from o-Alkynylacylarenes Rearrangements of Propargyl EstersSkeletal Rearrangement of 3-Butynyl-N-Oxides: (_)-Cermizine and (?)-LentiginosineEnyne Cyclizations Propargyl Claisen Rearrangement: Azadirachtin Gold-Catalyzed C?H Activation: (_)-Pterocarpan and Crassifolone Gold-Catalyzed Allylic Amination: (_)-AngustureineCatalytic Asymmetric Aldol Reaction of Isocyanoacetates and AldehydesGOLD-CATALYZED ADDITION REACTIONS TO ALLENESIntroduction Addition of Heteroatom Nucleophiles Addition of Carbon Nucleophiles Conclusion
About the author
A. St. K. Hashmi is Professor for Organic Chemistry at Stuttgart University. Born in Munich, Germany, he completed his studies at the LMU Munich, gaining his doctorate under the supervision of Günter Szeimies. During his post-doctorate at Stanford University, he worked with Barry M. Trost. His further postdoctoral work at the FU Berlin, Vienna University and Frankfurt University with Johann Mulzer and further activities at the University of Tasmania and Marburg University culminated in his position at Stuttgart University in 2001.
Summary
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.
Report
"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)
