Über die Autorin bzw. den Autor

SHIGEO NISHIMURA, DSc, is Professor Emeritus at the Tokyo University of Agriculture and Technology. He is a member of the Chemical Society of Japan and the Catalysis Society of Japan.

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A complete guide to the most important reduction method in organic synthesis

The most comprehensive reference in the field, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis provides synthetic chemists and chemical engineers in fine chemicals and pharmaceuticals with detailed experimental guidelines for heterogeneous catalytic hydrogenation. Organized by functional groups for ready reference and featuring detailed examples of hundreds of reactions, this handbook covers hydrogenations of alkenes, alkynes, aldehydes and ketones, nitriles, imines, nitro and nitroso compounds, carboxylic acids and esters, and aromatic and heterocyclic compounds. In addition, coverage includes the preparation of amines by reductive alkylation and the hydrogenolysis of a variety of compounds. Examples of hydrogenation of functional groups and reaction pathways are illustrated with numerous equations and schemes.

Practitioners will appreciate the plenitude of experimental details given for most of the reactions selected, including amounts of reagents and catalysts, reaction temperatures, hydrogen pressures, and reaction times. They will also find helpful the more than one hundred tables included throughout the book detailing the effects of key factors governing rate and selectivity, such as compound structure, the nature of catalysts and supports, and the nature of solvents. Researchers will benefit from the introductory chapters covering an array of hydrogenation catalysts, including nickel, cobalt, copper, iron, platinum group metals, rhenium, and other oxide and sulfide catalysts, as well as reactors and reaction conditions.

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A complete guide to the most important reduction method in organic synthesis

The most comprehensive reference in the field, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis provides synthetic chemists and chemical engineers in fine chemicals and pharmaceuticals with detailed experimental guidelines for heterogeneous catalytic hydrogenation. Organized by functional groups for ready reference and featuring detailed examples of hundreds of reactions, this handbook covers hydrogenations of alkenes, alkynes, aldehydes and ketones, nitriles, imines, nitro and nitroso compounds, carboxylic acids and esters, and aromatic and heterocyclic compounds. In addition, coverage includes the preparation of amines by reductive alkylation and the hydrogenolysis of a variety of compounds. Examples of hydrogenation of functional groups and reaction pathways are illustrated with numerous equations and schemes.

Practitioners will appreciate the plenitude of experimental details given for most of the reactions selected, including amounts of reagents and catalysts, reaction temperatures, hydrogen pressures, and reaction times. They will also find helpful the more than one hundred tables included throughout the book detailing the effects of key factors governing rate and selectivity, such as compound structure, the nature of catalysts and supports, and the nature of solvents. Researchers will benefit from the introductory chapters covering an array of hydrogenation catalysts, including nickel, cobalt, copper, iron, platinum group metals, rhenium, and other oxide and sulfide catalysts, as well as reactors and reaction conditions.

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Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis

John Wiley & Sons

Contents

Preface........................................................................................................................xi1 Hydrogenation Catalysts......................................................................................................11.1 Nickel Catalysts..........................................................................................................21.2 Cobalt Catalysts..........................................................................................................231.3 Copper Catalysts..........................................................................................................261.4 Iron Catalysts............................................................................................................281.5 Platinum Group Metal Catalysts............................................................................................291.6 Rhenium Catalysts.........................................................................................................421.7 The Oxide and Sulfide Catalysts of Transition Metals Other than Rhenium...................................................432 Reactors and Reaction Conditions.............................................................................................522.1 Reactors..................................................................................................................522.2 Reaction Conditions.......................................................................................................533 Hydrogenation of Alkenes.....................................................................................................643.1 Isolated Double Bonds: General Aspects....................................................................................653.2 Hydrogenation and Isomerization...........................................................................................683.3 Alkyl-Substituted Ethylenes...............................................................................................723.4 Selective Hydrogenation of Isolated Double Bonds..........................................................................773.5 Fatty Acid Esters and Glyceride Oils......................................................................................843.6 Conjugated Double Bonds...................................................................................................923.7 Stereochemistry of the Hydrogenation of Carbon-Carbon Double Bonds........................................................1003.8 Selective Hydrogenations in the Presence of Other Functional Groups.......................................................1194 Hydrogenation of Alkynes.....................................................................................................1484.1 Hydrogenation over Palladium Catalysts....................................................................................1494.2 Hydrogenation over Nickel Catalysts.......................................................................................1604.3 Hydrogenation over Iron Catalysts.........................................................................................1655 Hydrogenation of Aldehydes and Ketones.......................................................................................1705.1 Aldehydes.................................................................................................................1705.2 Hydrogenation of Unsaturated Aldehydes to Unsaturated Alcohols............................................................1785.3 Ketones...................................................................................................................1855.4 Stereochemistry of the Hydrogenation of Ketones...........................................................................2005.5 Mechanistic Aspects of the Hydrogenation of Ketones.......................................................................2186 Preparation of Amines by Reductive Alkylation................................................................................2266.1 Reductive Alkylation of Ammonia with Carbonyl Compounds...................................................................2266.2 Reductive Alkylation of Primary Amines with Carbonyl Compounds............................................................2366.3 Preparation of Tertiary Amines............................................................................................2416.4 Reductive Alkylation of Amine Precursors..................................................................................2466.5 Alkylation of Amines with Alcohols........................................................................................2476.6 Synthesis of Optically Active [alpha]-Amino Acids from [alpha]-Oxo Acids by Asymmetric Transamination.....................2486.7 Asymmetric Synthesis of 2-Substituted Cyclohexylamines....................................................................2507 Hydrogenation of Nitriles....................................................................................................2547.1 General Aspects...........................................................................................................2547.2 Hydrogenation to Primary Amines...........................................................................................2597.3 Hydrogenation of Dinitriles to Aminonitriles..............................................................................2657.4 Hydrogenation to Aldimines or Aldehydes...................................................................................2677.5 Hydrogenation to Secondary and Tertiary Amines............................................................................2707.6 Hydrogenation Accompanied by Side Reactions...............................................................................2738 Hydrogenation of Imines, Oximes, and Related Compounds.......................................................................2868.1 Imines....................................................................................................................2868.2 Oximes....................................................................................................................2908.3 Hydrazones and Azines.....................................................................................................3059 Hydrogenation of Nitro, Nitroso, and Related Compounds.......................................................................3159.1 Hydrogenation of Nitro Compounds: General Aspects.........................................................................3159.2 Aliphatic Nitro Compounds.................................................................................................3159.3 Aromatic Nitro Compounds..................................................................................................3329.4 Nitroso Compounds.........................................................................................................3639.5 N-Oxides..................................................................................................................3699.6 Other Nitrogen Functions Leading to the Formation of Amino Groups.........................................................37110 Hydrogenation of Carboxylic Acids, Esters, and Related Compounds............................................................38710.1...