Heterogeneous Catalysis in Sustainable Synthesis (Advances in Green and Sustainable Chemistry)

Heterogeneous Catalysis in Sustainable Synthesis is a practical guide to the use of solid catalysts in synthetic chemistry that focuses on environmentally benign applications. Collating essential information on solid catalysts into a single volume, it reveals how the efficient use of heterogeneous catalysts in synthetic chemistry can support sustainable applications. Beginning with a review of the fundamentals of heterogeneous catalytic synthesis, the book then explores the basic concepts of heterogeneous catalytic reactions from adsorption to catalyst poisons, the use of non-traditional activation methods, recommended solvents, the major types of both metal and non-metal solid catalysts, and applications of these catalysts in sustainable synthesis. Based on the extensive experience of its expert author, this book aims to encourage and support synthetic chemists in using solid catalysts in their own work, while also highlighting the important link between heterogeneous catalysis and sustainability to all those interested. 62f35485_Cover(full permission) Front-Matter_2022_Heterogeneous-Catalysis-in-Sustainable-Synthesis Front Matter Copyright_2022_Heterogeneous-Catalysis-in-Sustainable-Synthesis Copyright Contents Preface_2022_Heterogeneous-Catalysis-in-Sustainable-Synthesis Preface Chapter-1---Heterogeneous-catalysis-for-organic_2022_Heterogeneous-Catalysis Heterogeneous catalysis for organic synthesis: Historical background and fundamentals Introduction and historical background Catalysis Fundamentals and basic definitions Catalyst and catalytic cycle Activation energy Other definitions Heterogeneous catalysis Catalytic surfaces Physical and chemical adsorption The active site of solid catalysts Anchoring effects Experimental variables Catalytic reactors Conclusions and outlook References Chapter-2---Solid-catalysts-for-environm_2022_Heterogeneous-Catalysis-in-Sus Solid catalysts for environmentally benign synthesis Introduction Metal catalysts Unsupported metals Bulk or massive metals Metal “blacks” Skeletal metals Noble metal oxides and hydroxides Amorphous metal alloys Supported metal catalyst Catalyst supports SiO2 Al2O3 Other metal oxides and metal carbonates Magnetic catalyst supports Carbon-based supports Polymeric materials Biomass-based materials Self-supported catalysts Heterogenized metal complexes and organocatalysts Metal nanoparticle-based catalysts Nonmetallic catalysts Metal oxides Heteropoly acids Clays Zeolites Ion exchange resins Metal-organic frameworks Other nonmetallic catalytic materials Molecular sieves, pillared layer solids, and other mesoporous solids Composites and related materials Conclusions and outlook References Chapter-3---Application-of-heterogeneous-catalysis_2022_Heterogeneous-Cataly Application of heterogeneous catalysis in the development of environmentally benign synthetic processes References Chapter-3-1---Hydrogenatio_2022_Heterogeneous-Catalysis-in-Sustainable-Synth Hydrogenation Introduction Carbon-carbon multiple bond hydrogenations: Alkenes, alkynes, dienes Hydrogenation of aromatic and heteroaromatic compounds Reduction of carbonyl compounds by heterogeneous catalytic hydrogenation: Aldehydes, ketones, and carboxylic acid d ... Hydrogenation of nitrogen-containing groups: NO, NN, CN, and CN groups Hydrogenation of the nitro group Hydrogenation of nitriles Hydrogenation of imines Hydrogenation of azides Chemo- and regioselective hydrogenation of compounds with multiple hydrogenation sensitive groups Selective CC bond hydrogenation of α,β-unsaturated carbonyl compounds Selective CO reduction of α,β-unsaturated carbonyl compounds Complete hydrogenation of multiple functional groups using the same catalytic system Heterogeneous catalytic hydrogenations by nonconventional activation methods Microwave-assisted hydrogenations Ultrasound-assisted hydrogenations Conclusions and outlook References Chapter-3-10---Asymmetric-synthesis-by_2022_Heterogeneous-Catalysis-in-Susta Asymmetric synthesis by solid catalysts Introduction Oxidation reactions Epoxidation Dihydroxylation Other oxidations Hydrogenation Reduction of carbonyl compounds Reduction of mono-carbonyl compounds Reduction of 1,2-dicarbonyl compounds Reduction of 1,3-dicarbonyl compounds Reductive alkylation Reduction of CC double bonds Aldol-reaction and related chemistry Aldol reactions Michael additions Henry reactions Multicomponent and various other reactions Multicomponent reactions Cascade and tandem reactions Other reactions Conclusions and outlook References Chapter-3-2---Heterogeneous-catalytic-hydro_2022_Heterogeneous-Catalysis-in- Heterogeneous catalytic hydrogenolysis of organic compounds Introduction CC bonds CO bonds CN bonds C-halogen bonds—Dehalogenation NN and NO bonds CS bonds Hydrogenolysis of C-other elements (Si, metals) bonds Hydrogenolysis of biomass-related compounds Hydrogenolysis of biomass-derived oxygen-containing heterocycles Hydrogenolysis of biomass-derived other oxygen-containing compounds Conclusions and outlook References Chapter-3-3---Heterogeneous-catalyt_2022_Heterogeneous-Catalysis-in-Sustaina Heterogeneous catalytic oxidations Introduction Epoxidation reactions Dihydroxylation reactions Dihydroxylations with osmium Dihydroxylations with metals other than osmium Wacker-type oxidation reactions Oxidative cleavage of hydrocarbons Cleavage to generate aldehydes and ketones Cleavage to generate carboxylic acids and esters Other oxidative cleavage reactions Oxidation of CO and CN bonds Oxidation of CO bonds Oxidation of CN bonds Dehydrogenation and aromatization of CC and CX bonds Conclusions and outlook References Chapter-3-4---Metathesis-by-heterogen_2022_Heterogeneous-Catalysis-in-Sustai Metathesis by heterogeneous catalysts Introduction Cross-metathesis Ring-closing metathesis Ring-opening metathesis Alkyne metathesis Heterogeneous catalytic asymmetric metathesis Metathesis applied to bioderived alkenes Conclusions and outlook References Chapter-3-5---Friedel-Crafts-and-related-re_2022_Heterogeneous-Catalysis-in- Friedel-Crafts and related reactions catalyzed by solid acids Introduction Alkylation, hydroxyalkylation Alkylations with hydrocarbons Alkylations with alcohols, ethers, aldehydes, and ketones Alkylations with alkyl halides Hydroxyalkylations Intramolecular transalkylations—Rearrangements Acylation Acylations with carboxylic acids Acylations with activated carboxylic acid derivatives Intramolecular transacylations—Rearrangements Friedel-Crafts cycliacyalkylations Halogenation Nitration Sulfonation Conclusions and outlook References Chapter-3-6---Cross-coupling-reactions-for-_2022_Heterogeneous-Catalysis-in- Cross-coupling reactions for environmentally benign synthesis Introduction The Heck coupling Heck reactions using a heterogeneous catalyst in solution Solvent-free Heck reactions Heck reactions without palladium The Suzuki coupling Palladium-catalyzed heterogeneous Suzuki coupling reactions Palladium-free heterogeneous catalytic Suzuki coupling reactions The Hiyama coupling The Negishi coupling The Kumada coupling The Sonogashira coupling The Tsuji-Trost allylation Coupling reactions not involving a C  C bond formation C  N bond-forming reactions C  O bond-forming reactions C  S bond-forming reactions Conclusions and outlook References Chapter-3-7---Multicomponent-re_2022_Heterogeneous-Catalysis-in-Sustainable- Multicomponent reactions Introduction Carbonyl-based multicomponent reactions Formation of 6-membered rings with multicomponent reactions Formation of 5-membered rings with multicomponent reactions Formation of aliphatic bonds Isocyanide-based reactions Isocyanide-based MCRs for the preparation of 5-membered rings Isocyanide-based MCRs for the preparation of 5- and 6-membered heterocycles Aliphatic bond formation Conclusions and outlook References Chapter-3-8---Ring-transformations-by-he_2022_Heterogeneous-Catalysis-in-Sus Ring transformations by heterogeneous catalysis Introduction Cyclization Intermolecular cyclization reactions Diels-Alder and hetero-Diels-Alder reactions Heterogeneous catalytic synthesis of six-membered rings Pyrazines and piperazines Pyridines Tetrahydropyranols Heterogeneous catalytic synthesis of five-membered rings Pyrroles Furans The Huisgen 1,3-dipolar cycloaddition Application of phenylenediamines and/or diazotization Oxazolidinones/oxindoles Pyrazoles Intramolecular cyclization reactions Heterogeneous catalytic synthesis of five-membered rings The Nazarov cyclization Tetrahydrofurans Heterogeneous catalytic synthesis of six-membered rings Isopulegol Ionones Terpenoids Quinolines/isoquinolines Ring opening reactions Ring opening of small heterocycles Ring opening of epoxides Synthesis of β-substituted alcohols Synthesis of carbonyl compounds Synthesis of cyclic carbonates Ring opening of aziridines Ring opening polymerization Other types of ring opening reactions Conclusions and outlook References Chapter-3-9---Heterogeneous-catalytic-rearra_2022_Heterogeneous-Catalysis-in Heterogeneous catalytic rearrangements and other transformations Rearrangements Beckmann rearrangement Fries rearrangement Epoxide rearrangements Ferrier rearrangement Johnson-Claisen rearrangement The ortho-Claisen-rearrangement Benzylimine-benzaldimine rearrangement Pinacol rearrangement Baeyer-Villiger oxidation Aldol and related reactions The aldol reaction Mukaiyama reaction Condensations Schiff-base formation Knoevenagel condensation Pechmann condensation Aldol condensation Hydrolysis Hydrolysis of cellulose Introduction and removal of protecting groups Hydroformylations Conclusions and outlook References Index_2022_Heterogeneous-Catalysis-in-Sustainable-Synthesis Index A B C D E F G H I J K L M N O P Q R S T U V W X Z Back_Cover