Selective Hydrogenation of Functionalized Hydrocarbons

Abstract

The sections in this article are Introduction Significance of Catalytic Methods in Organic Synthesis Guidelines for the Selection of a Catalytic Hydrogenation System Introduction General Approaches to Tuning Catalytic Processes A Selectivity in Catalytic Hydrogenation: a Challenge for Organic Chemists B Concepts and Tools Useful for Catalytic Hydrogenation General Strategy and Experiment Planning Catalyst Selection A Metal Selection B Catalyst Support C Catalyst Particle Size and Morphology D Porosity of the Support and Location of the Metal E Metal Dispersion and Metal Crystallite Size F Other Factors Selection of the Reaction Medium A Solvent B Acids and Bases C Catalyst Modifiers Reaction Conditions A Temperature B Hydrogen Pressure C Substrate Concentration D Catalyst Loading and Substrate to Catalyst Ratio E Degree of Conversion Chemoselectivity in Catalytic Hydrogenation Selective Hydrogenation of Functionalized Aromatic Nitro Compounds Introduction Mechanism of Nitroarene Reductions Practical Aspects A Catalysts B Reaction Medium and Conditions C Safety and Health Aspects a Hazards Related to Hydrogen b Hazards Related to the Catalyst c Hazards Due to the Hydrogenation Reaction d Hazards Due to the High Decomposition Energy of Aromatic Nitro Compounds and some Intermediates e Toxicity D Hydrogenation Equipment Selective Hydrogenation of Halogenated Nitroarenes A Introduction B Catalysts a Modified Catalysts b In Situ Modification New Catalyst Systems for the Hydrogenation of a Nitro Group in the Presence of Reducible Functional Groups A Lead‐Modified Platinum Catalysts: the “Lindlar Approach” B H 3 PO 2 ‐Modified Pt Catalysts in the Presence of Vanadium Promoters Hydroxylamine Accumulation Selective Semihydrogenation of Alkynes Introduction Chemical and Physical Background for Selectivity in Alkyne Hydrogenation Tools to Achieve Selectivity for Alkene Formation A Metal Selection B Chemical Composition of the Support C Metal Location D Metal Dispersion and Crystallite Size E Catalyst Modifiers F Solvent G Temperature H Hydrogen Pressure I Substrate Concentration J Catalyst/Substrate Ratio K Agitation L Degree of Conversion Selective Catalytic Debenzylation Introduction Catalysts Used for Selective Debenzylation Influence of Reaction Conditions A Hydrogen Source and Pressure B Solvent, Modifiers and Promoters Selective Removal of Benzyl Groups A Selective Removal of O ‐Benzyl Groups in the Presence of other O ‐Benzyl Groups B Selective Removal of O ‐Benzyl Groups in the Presence of N ‐Benzyl Groups C Selective Removal of O ‐Benzyl Groups in the Presence of other Reducible Functions D Selective Removal of N ‐Benzyl Groups in the Presence of other N ‐Benzyl Groups E Selective Removal of N ‐Benzyl Groups in the Presence of other Reducible Functions F New Protecting Groups Mechanism of Debenzylation and Mode of Action of Modifiers Stereoselective Reactions Diastereoselective Hydrogenation Enantioselective Hydrogenation Chemoselective Hydrogenation of Nitriles Primary Amine Formation Chemoselective Hydrogenation of Unsaturated Nitriles

Olefin Purification and Selective Hydrogenation of Alkynes with Low Loaded Pd Nanoparticle Catalysts

“…Selective hydrogenation is a key process for the elimination of impurities or the obtaining of products with high added value. All selective hydrogenations are of great interest considering economic and ecological aspects 2,8,9 . Selective hydrogenation of alkynes to alkenes represents one of the most important steps in fine chemicals manufacture 10 .…”

Ligand-Promoted Iridium-Catalyzed Transfer Hydrogenation of Terminal Alkynes with Ethanol and Its Application

“…Transfer hydrogenation of unsaturated compounds has attracted much attention due to its widespread use in the synthesis of synthetic intermediates, natural products, fragrances, pharmaceuticals, and agrochemical products . To date, several catalytic systems applicable to alkyne transfer hydrogenation, represented by Lindlar reduction, have been reported. Among all the transfer hydrogenation, the metal-catalyzed transfer semireduction is attracting much attention because of its critical advantage over the conventional semihydrogenation method, which suffers from problems with overreduction as well as safety concerns .…”

Highly-Ordered PdIn Intermetallic Nanostructures Obtained from Heterobimetallic Acetate Complex: Formation and Catalytic Properties in Diphenylacetylene Hydrogenation

“…This reaction is of significant importance because its products (cis-/trans-olefins) play a key role as source materials for the food and pharmaceutical industry, domestic chemicals, light-emitting diodes, liquid-crystal displays, etc. [ 33 , 34 , 35 , 36 ].…”