Modern Gold Catalyzed Synthesis

Modern Gold Catalyzed Synthesis

By: A. Stephen K. Hashmi (editor), F. Dean Toste (editor)Hardback

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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 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.

About Author

Stephen Hashmi is professor for Organic Chemistry at University of Heidelberg, Germany. He obtained his academic degrees from Ludwig-Maximilians-Universitat Munchen, after his postdoctoral studies with Barry M. Trost at Stanford University he started his Habilitation at Freie Universitat Berlin with Johann Mulzer. During that time he followed Prof. Mulzer to Johann Wolfgang Goethe-Universitat Franfurt and Universitat Wien. He then returned to Frankfurt to finish his Habilitation. After the stations at University of Tasmania, Australia, Universitat Marburg, and Universitat Stuttgart, he was appointed a full professorship at Heidelberg University, where he is also involved in the Catalysis Research Laboratory (CaRLa). He received a number of awards, including a Karl-Zieger fellowship, the ORCHEM prize for natural scientists and the Hector research award. F. Dean Toste was born in Terceira, Azores, Portugal but soon moved to Toronto Canada. He received his B.Sc. and M.Sc. degrees in chemistry from the University of Toronto, Canada where he worked with Prof. Ian W. J. Still. In 1995, he began his doctoral studies at Stanford University under the direction of Professor Barry M. Trost. Following postdoctoral studies with Professor Robert H. Grubbs at Caltech, he joined the faculty at the University of California, Berkeley in 2002, and was promoted to Associate Professor in 2006 and Professor in 2009. Professor Toste?s honors include an Alfred P. Sloan Research Fellowship, the Cope Scholar Award and the E. J. Corey Award from the American Chemical Society, BASF Catalysis Award, the OMCOS and Thieme Award from IUPAC, the Merck Award from the Royal Society of Chemistry, the Mukaiyama Award, the Tetrahedron Young Investigator Award and numerous awards from the pharmaceutical industry.


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

Product Details

  • ISBN13: 9783527319527
  • Format: Hardback
  • Number Of Pages: 418
  • ID: 9783527319527
  • weight: 944
  • ISBN10: 3527319522

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