Organic Synthesis with Palladium Compounds

ISBN-13: 9783642674778 / Angielski / Miękka / 2011 / 210 str.

Jiro Tsuji

Opis

Around 30 years ago the transition metal chemistry received great impulses. In the focus have been reactions of nickel and cobalt and herein especially their carbonyls. Also industrial processes have been developed. When the technical oxidation of ethylene with palladium chloride had been discovered, and a great number oflaboratory reactions, many groups have turned towards this subject. Apart from two important industrial processes - acetaldehyde and vinylacetate from ethylene - a great number of conversions and catalytic reactions with palladium compounds have been researched. Their mechanisms have been cleared up and have con tributed to a better understanding of the complex chemistry of palladium. Last but not least these reactions have also served for more understanding of organic transition metal compounds and catalyses in general. Numerous conventional reactions appear today in a different light. The effects of co-"

Spis treści

I. Introduction.- II. Palladium Compounds and Complexes Useful in Organic Synthesis.- III. Oxidation Reactions with Pd2+ Compounds.- 1. Introduction.- 2. Reactions of Olefins.- a. Introduction.- b. Reactions of Water (Wacker Reaction).- c. Reactions of Alcohols, Phenols and Other Hydroxy Compounds.- d. Reactions of Carboxylic Acids.- e. Oxidative Carbonylation Reactions.- f. Reactions of Aromatic Compounds.- g. Reactions of Carbanions.- h. Reactions of Amines.- i. Reactions of Hydrogen Cyanide and Chloride.- j. Oxidative Coupling Reactions.- k. Reactions of Alkynes.- 3. Synthetic Reactions with ?-Allyl Complexes.- a. Introduction.- b. Methods of Preparing ?-Allylpalladium Complexes.- c. Reactions of Carbon Monoxide and Isocyanides.- d. Reactions of Active Methylene Compounds.- e. Reactions of Other Nucleophiles.- 4. Reactions of Aromatic Compounds.- 5. Synthetic Reactions by Transmetallation of Organomercury Compounds and Related Reactions.- 6. Synthetic Reactions Based on Chelation of Heteroatoms.- a. Ortho-Palladation of Aromatic Compounds.- b. Reactions of Allylic and Homoallylic Amines and Sulfides.- 7. Dehydrogenation Reactions.- 8. Reactions of Alkynes.- 9. Reactions of Alcohols and Carbon Monoxide.- 10. Miscellaneous Reactions.- IV. Catalytic Reactions.- 1. Introduction.- 2. Reactions of Olefins.- a. Carbonylation Reactions.- b. Addition Reactions (Oligomerization and Co-Oligomerization).- c. Hydrosilylation Reactions.- d. Miscellaneous Reactions.- 3. Reactions of Conjugated Dienes.- a. Introduction.- b. Oligomerization.- c. Telomerization with Water, Alcohols and Phenols.- d. Telomerization with Carboxylic Acids.- e. Telomerization with Ammonia and Amines.- f. Telomerization with Enamines.- g. Telomerization with Active Methylene and Methyne Compounds.- h. Reactions of Silicon Compounds.- i. Carbonylation Reactions.- j. Reactions of Phenylhydrazones and Oximes.- k. Cocyclization Reactions.- 1. Reactions of Carbon Dioxide.- m. Application of Butadiene Telomers to Natural Product Syntheses.- n. Dimerization and Telomerization of Isoprene and Other Dienes.- 4. Reactions of Allene.- 5. Reactions of Allyl Ethers, Esters, and Alcohols.- 6. Reactions of Alkenyl Ethers and Esters.- 7. Reactions of Organic Halides.- a. Allylic Halides.- b. Aryl Halides.- c. Alkenyl Halides.- d. Acyl Halides.- e. Reactions of ?-Halo Ketones and Benzyl Halides.- 8. Decarbonylation of Aldehydes.- 9. Reaction of Alkynes.- a. Carbonylation Reactions.- b. Addition and Cyclization Reactions.- c. Reactions with Silicon Compounds.- d. Miscellaneous Reaction.- 10. Reactions of Silicon Compounds.- 11. Reactions of Amines.- 12. Reactions of Isocyanides.- 13. Palladium Catalyzed Decomposition of Azo Compounds, Azides and Peroxides.- 14. Rearrangement Reactions Promoted by PdC12.- 15. Miscellaneous Reactions of Carbon Monoxide and Carbon Dioxide.- 16. Reductions.- 17. Miscellaneous Reactions.- References.