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This book collects articles published in a Special Issue of Molecules entitled "Organic Synthesis via Transition Metal-Catalysis". Transition metal catalysis is a powerful methodology for the direct synthesis of functionalized, high value-added molecules by the assembly of simple units in one step, and is acquiring increasing importance in modern organic synthesis. The book presents seven papers overall, two reviews and five original research articles, dealing with Pd-catalyzed arylation, Rh-catalyzed synthesis of organosulfur compounds, Rh-catalyzed reductive hydroformylation, V-catalyzed oxidation of hydrocarbons, and Zn-, Pd- and Rh-catalyzed cyclization processes, leading to heterocyclic derivatives.

palladium --- indole --- indomethacin --- C-H functionalization --- sulfoximide --- C–H activation --- benzothiazine --- rhodium --- catalysis --- synthesis --- organosulfur compounds --- S-S bond cleavage --- chemical equilibrium --- reversible reaction --- alkynes --- annulation --- benzimidazoxazinones --- heterocycles --- polycyclic heterocycles --- heterocyclization --- zinc --- direct arylation --- pincer complexes --- vanadium(IV) complexes --- biological activity --- catalytic properties --- 8-hydroxyquinoline --- cytotoxicity studies --- hydroformylation --- hydrogenation --- tandem reaction --- n/a --- C-H activation

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Nitro chemistry plays an important role in organic synthesis to construct new frameworks. This is due to the diverse properties of the nitro group. The strong electron-withdrawing ability of the nitro group reduces the electron density of the scaffold, facilitating reactions with nucleophiles or electron transfer. In addition, the -hydrogen of the nitro group is highly acidic, giving a stable anion, which facilitates reactions with both electrophilic and nucleophilic reagents. In addition, the nitro group also serves as a good leaving group, which facilitates transformation to a wide variety of functional groups. Despite the substantial contributions of many researchers, nitro chemistry is still an exciting and challenging research area. This book brings together recent original research and review articles contributed by an international team of leading experts and pioneers in organic synthesis using nitro groups. It is sure to provide useful information and promising insights for researchers.

Research & information: general --- nitro --- pyridone --- 1-methyl-2-quinolone --- cycloaddition --- direct functionalization --- perylenediimide --- nitro group --- organic materials --- Phenacylation of beta-nitropyridin-2-ones --- 8-nitro-5-RO-indolizines --- oxazole-pyrrole ring transformation --- conjugate addition --- dihydrofuran --- 1,3-dicarbonyl compound --- enolate --- isoxazoline N-oxide --- nitroketone --- nitronate --- nucleophilic substitution --- nitropyridines --- isoxazolo[4,3-b]pyridines --- 1,4-dihydropyridines --- nucleophilic addition --- Diels-Alder reaction --- dearomatization --- hexapyrrolohexaazacoronene --- nitration --- SNAr substitution --- ICT character --- aromaticity --- C–H functionalization --- total synthesis --- pyrrolidines --- anchimeric assistance --- epimerization --- PDE4 inhibitors --- 1,3-Dipole --- electron-withdrawing ability --- electrophilicity --- nucleophilicity

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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.

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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In this Special Issue, recent advances in cross-coupling reactions are presented in the form of original research articles, reviews, and short communications. These contributions cover different topics in this area, including novel coupling reactions, reaction conditions, synthetic alternatives, metal ligands, and applications for new pharmaceutical compounds and organic materials. In particular, the reviews deal with methodologies such as the synthesis of diarylketones through palladium catalysis and the most relevant examples of Suzuki–Miyaura and Buchwald–Hartwig coupling reactions in the synthesis of bioactive compounds. The synthetic utility of cross-coupling reactions for the synthesis of medium-size rings and the utility of Stille and Suzuki coupling reactions for the synthesis of new molecular machines based on sterically hindered anthracenyl trypticenyl units are also summarized. The original research articles present the synthesis of 2-alkynylpyrrols by inverse Sonogashira coupling and the synthesis of indoles under oxidative dearomative cross-dehydrogenative conditions. The efficient combination of iridium-catalyzed C–H borylation of aryl halides with the Sonogashira coupling and a sequential iridium-catalyzed borylation of NH-free pyrroles followed by a Suzuki–Miyaura reaction are included. The synthesis of aryl propionic acids, a common structural motif in medicinal chemistry, and the synthesis of new organic dyes are also covered.

Research & information: general --- cross coupling --- dearomatization --- C-H functionalization --- indolin-3-ones --- dimerization and trimerization of indoles --- C–H borylation --- Sonogashira cross-coupling --- borylated aryl alkynes --- one-pot reaction --- restricted rotations --- M(CO)3 tripods --- molecular brakes and gears --- X-ray --- V-T NMR --- borylation --- Suzuki coupling --- NH-Free --- 5-aryl pyrrole-2-carboxylates --- iridium-catalyzed --- heteroaryl substituted pyrroles --- 2,3′-bipyrrole --- electrophilic haloacetylenes --- pyrroles --- ethynylpyrroles --- furans --- thiophenes --- pyrazoles --- Al2O3 --- transition-metal catalysis --- intramolecular cyclization --- medium-sized heterocycles --- C-H activation --- acylation --- palladium --- arenes --- heteroarenes --- indigo dyes --- DSSC --- synthesis --- spectroscopy --- Heck reaction --- styrene --- methoxycarbonylation --- profene --- cross-coupling reactions --- C-C bond forming reactions --- C-Heteroatom bond forming reactions --- clinical candidate --- DNA-encoded libraries --- cyclopeptides --- allosteric modulators --- PROTAC --- catalysis in water --- C–C cross-coupling --- Suzuki–Miyaura reaction --- sulfonated salan --- n/a --- C-H borylation --- 2,3'-bipyrrole --- C-C cross-coupling --- Suzuki-Miyaura reaction

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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