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Transition metal-catalyzed reactions play a key role in many transformations of synthetic organic chemistry. For most of these reactions, noble metals, for example, palladium, have been used as catalysts. Over the last two decades, more and more first row transition metals have been applied as catalysts for organic reactions, with iron taking the center stage. The driving forces behind this development are not only the high costs for the noble metals but also their toxicity. Iron is the most abundant transition metal in the Earth’s crust, and thus, it is considerably cheaper than the precious noble metals. Moreover, iron compounds are involved in many biological processes, and thus, iron exhibits a low toxicity. Because of this low toxicity, iron-catalyzed reactions are important for an environmentally benign sustainable chemistry. However, iron catalysts are not only investigated to replace noble metals; they offer many applications in synthesis beyond those of classical noble metal catalysts. Several articles of the present book emphasize the complementarity of iron-catalyzed reactions as compared to reactions catalyzed by noble metals. The book shows intriguing recent developments and the current standing of iron-catalyzed reactions as well as applications to organic synthesis.

Research & information: general --- iron --- cross-coupling --- aryl esters --- C–O activation --- Fe-catalysis --- Kumada cross-coupling --- iron complexes --- hydrogen transfer --- reductive amination --- alcohols --- amines --- decarbonylation --- alkylation --- spirocyclization --- aldehyde --- cinnamamide --- iron catalysis --- bis-(aryl)manganese --- alkenyl halides --- ate iron(II) complex --- asymmetric catalysis --- nitrogen ligand --- oxidative coupling --- BINOL synthesis --- carbene --- diazoalkane --- C-H functionalization --- catalysis --- borylation --- Iron --- C-H functionalisation --- pinacolborane --- photochemistry --- amidation --- iron(III) chloride --- amides --- esters --- solvent-free --- iron-catalysis --- carboazidation --- β-methyl scission --- radical --- DFT --- organic synthesis --- C-H activation --- C-C coupling --- α-alkenylation --- dehydrogenative coupling --- sustainability --- naphthidines --- fluorescence --- iron catalyst --- ATRP --- controlled radical polymerization --- external stimuli --- asymmetric transfer hydrogenation --- density functional theory --- bifunctional catalyst --- haloalkane coupling --- Grignard reagent --- FeI/FeII/FeIII mechanism

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The amide bond represents a privileged motif in chemistry. The recent years have witnessed an explosion of interest in the development of new chemical transformations of amides. These developments cover an impressive range of catalytic N–C bond activation in electrophilic, Lewis acid, radical, and nucleophilic reaction pathways, among other transformations. Equally relevant are structural and theoretical studies that provide the basis for chemoselective manipulation of amidic resonance. This monograph on amide bonds offers a broad survey of recent advances in activation of amides and addresses various approaches in the field.

N-heterocyclic carbene --- non planar amide --- ruthenium (Ru) --- physical organic chemistry --- gemcitabine prodrug --- pyramidal amides --- bridged sultams --- catalysis --- dipeptides --- N-(1-naphthyl)acetamide --- C-N ? bond cleavage --- steric effects --- peptide bond cleavage --- transition-metal-free --- palladium --- N-heterocyclic carbenes (NHCs) --- addition reaction --- C–O activation --- rhodium --- metal complexes --- carbanions --- thioamidation --- amide bond --- intramolecular catalysis --- antiviral activity --- additivity principle --- pre-catalysts --- C–N bond cleavage --- bridged lactams --- C–H acidity --- arynes --- twisted amides --- organic synthesis --- amination --- Suzuki-Miyaura --- tert-butyl --- cyclopentadienyl complexes --- C-S formation --- enzymes --- DFT study --- sulfonamide bond --- N --- HERON reaction --- primaquine --- entropy --- amide activation --- amidation --- synthesis --- amide hydrolysis --- carbonylicity --- amide bond activation --- amide bond resonance --- aminosulfonylation --- molecular dynamics --- model compound --- in situ --- amide --- homogeneous catalysis --- heterocycles --- anomeric effect --- multi-component coupling reaction --- kinetic --- excited state --- C–H bond cleavage --- palladium catalysis --- amides --- thiourea --- formylation --- alkynes --- cis/trans isomerization --- amide C–N bond activation --- intein --- C-H functionalization --- succindiamide --- amide bonds --- crown ether --- aminoacylation --- directing groups --- cytostatic activity --- reaction thermodynamics --- acyl transfer --- transition metals --- N-dimethylformamide --- DMAc --- acylative cross-coupling --- C-H/C-N activation --- nickel catalysis --- antibacterial screening --- sodium --- aryl thioamides --- Winkler-Dunitz parameters --- catalyst --- N-dimethylacetamide --- base-catalyed hydrolysis --- nitrogen heterocycles --- cross-coupling --- insertion --- amidicity --- nitro-aci tautomerism --- activation --- carbonylation --- transamidation --- amine --- distortion --- Pd-catalysis --- rotational barrier energy --- hypersensitivity --- N–C activation --- metabolic stability --- [2+2+2] annulation --- twisted amide --- protease --- cyanation --- amide resonance --- trialkylborane --- catalysts --- biofilm eradication --- pharmacokinetics --- pancreatic cancer cells --- DMF --- aryl esters --- Michael acceptor --- fumardiamide --- water solvation --- ester bond activation --- cyclization --- nuclear magnetic resonance --- secondary amides --- reaction mechanism --- density functional theory --- density-functional theory --- amino acid transporters