Reduction in Organic Synthesis

Description

This book discusses some of the reduction agents and processes involved in organic synthesis such as catalytic hydrogenation, homogeneous catalytic hydrogenation, asymmetric catalytic hydrogenations, hydride transfer reagents, dissolving metal reductions, and non-metallic reducing agents. It further covers the topics of photochemical reductions, enzymatic or microbial reduction, reductions of specific type of organic compounds including hydrocarbons, hydrogenolysis, enzymatic or microbial reduction, and some reductions under benign condition. This book is of immense use to undergraduate and postgraduate students of organic chemistry. It is also a useful reference book for researchers involved in organic synthesis. Cover Half Title Reduction in Organic Synthesis Copyright Preface Contents 1. Introduction References 2. Different Types of Reducing Agents 2.1 Catalytic Hydrogenation 2.1.1 Heterogeneous Catalytic Hydrogenation Platinum Palladium Rhodium Nickel Miscellaneous heterogeneous catalysts Adkins catalysts Copper chromite Zinc chromite 2.1.2 Homogeneous Catalytic Hydrogenation 2.1.3 Asymmetric Homogeneous Catalytic Hydrogenations 2.2 Hydride-Transfer Reagents 2.2.1 Aluminium Alkoxides 2.2.2 Lithium Aluminium Hydride 2.2.3 Sodium Borohydride 2.2.4 Di-isobutylaluminium Hydride (DIBAL) 2.2.5 Sodium Cyanoborohydride 2.2.6 Trialkylborohydrides 2.2.7 Borane and Dialkylboranes 2.3 Dissolving Metal Reductions 2.3.1 Electrolytic Reduction 2.3.2 Reduction with Sodium 2.3.2.1 Sodium-alcohol 2.3.2.2 Sodium-liquid Ammonia 2.3.2.3 Sodium Amalgam 2.3.2.4 Sodium and Xylene 2.3.2.5 Salts of Sodium 2.3.3 Reductions with Magnesium 2.3.4 Reductions with Aluminium 2.3.5 Reductions with Zinc 2.3.6 Reductions with Iron 2.3.7 Reductions with Tin and Its Compounds 2.4 Non-metallic Reducing Agents 2.4.1 Reductions with Hydrogen Iodide 2.4.2 Reductions with Hydrogen Sulfide 2.4.3 Reductions with Sulphur Dioxide 2.4.4 Reductions with Dimethly Sulfide 2.4.5 Reductions with Hydrazine 2.4.6 Reductions with Diimide 2.4.7 Reductions with Silanes 2.4.8 Reductions with Formic Acid 2.5. Photochemical Reductions 2.6. Enzymatic or Microbial Reductions References 3. Reduction of Specific Types of Organic Compounds 3.1 Reduction of Hydrocarbons 3.1.1 Reduction of Alkanes and Cycloalkanes 3.1.2 Reduction of Alkenes and Cycloalkenes (A) Reduction of Alkenes (B) Reduction of Cycloalkenes 3.1.3 Reduction of Dienes 3.1.4 Reduction of Alkynes and Cycloalkynes 3.1.5 Reduction of Aromatic Compounds 3.1.6 Reduction of Condensed Aromatic Hydrocarbons 3.1.7 Reduction of Heterocyclic Compounds 3.2 Reduction of Alcohols and Phenols 3.3 Reduction of Aldehydes 3.4 Reduction of Ketones 3.5 Reduction of Carboxylic Acids and Its Derivatives 3.6 Reduction of Nitro Compounds 3.7 Reduction of Nitriles References 4. Hydrogenolysis 4.1 Hydrogenolysis of C–X Bond 4.2 Hydrogenolysis of C–O Bond 4.3 Reductive Cleavage of a Carbon Oxygen Double Bond 4.4 Reductive Cleavage Carbon-Nitrogen Bond 4.5 Reductive Cleavage of Carbon-Sulphur Bonds References 5. Enzymatic or Microbial Reduction 5.1 Reduction of β-Ketoesters 5.2 Reduction of Ketones and Aldehydes References 6. Some Reductions under Benign Conditions 6.1 Introduction 6.2 Reduction of Carbon-Carbon Double Bonds 6.3 Reduction of Carbon-Carbon Triple Bonds 6.4 Reduction of Carbonyl Compounds 6.5 Reduction of Esters 6.6 Reduction of Aromatic Rings References Suggested Readings Index