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Metallic oxides --- Catalysis --- Transition metal catalysis
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Transition metal-catalyzed cross-coupling reactions have proved to be powerful tools for carbon–carbon as well as carbon–heteroatom bond formation in the development of synthetic methodologies for applications ranging from pharmaceuticals to materials. This book, consisting of an editorial, two reviews and two articles, focuses on recent promising research and novel trends in the field of cross-coupling reactions, employing a range of different catalysts. A review by Kostas and Steele provides a survey of the research in the area of cross-coupling catalytic reactions with transition metal complexes based on the thiosemicarbazone unit and a discussion of the prospects for future developments. Another review by Polychronopoulou, Shaya and co-authors describes the progress made over the 21st century concerning the utilization of C(sp3)–organoboranes as partners in metal-catalyzed C(sp3)–C(sp2) cross-couplings, such as B-alkyl Suzuki–Miyaura reactions. The article by Waldvogel, Breinbauer and co-authors demonstrates for the first time the synthetic potential of combining the electro-oxidative dehydrogenative cross coupling of ortho-substituted phenols with Pd-catalyzed cross-coupling reactions. In the second article, Štĕpnička and co-workers describe the preparation of palladium catalysts deposited over silica gel-bearing composite amide-donor functional moieties on the surface, which were evaluated in the Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes.
Technology: general issues --- Suzuki-Miyaura cross-couplings --- C(sp3) -C(sp2) --- alkylboron reagents --- metal catalysis --- alpha-helix --- anode --- CH-activation --- cross-coupling --- electrosynthesis --- oligoarene --- peptidomimetics --- phenol --- protein-protein interactions --- triflate --- thiosemicarbazone --- metal complex --- transition metal catalysis --- cross-coupling reaction --- Heck reaction --- Suzuki reaction --- Sonogashira reaction --- Kumada reaction --- Buchwald-Hartwig reaction --- deposited catalysts --- palladium --- functional amides --- alkynyl ketone synthesis --- Suzuki-Miyaura cross-couplings --- C(sp3) -C(sp2) --- alkylboron reagents --- metal catalysis --- alpha-helix --- anode --- CH-activation --- cross-coupling --- electrosynthesis --- oligoarene --- peptidomimetics --- phenol --- protein-protein interactions --- triflate --- thiosemicarbazone --- metal complex --- transition metal catalysis --- cross-coupling reaction --- Heck reaction --- Suzuki reaction --- Sonogashira reaction --- Kumada reaction --- Buchwald-Hartwig reaction --- deposited catalysts --- palladium --- functional amides --- alkynyl ketone synthesis
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Transition metal-catalyzed cross-coupling reactions have proved to be powerful tools for carbon–carbon as well as carbon–heteroatom bond formation in the development of synthetic methodologies for applications ranging from pharmaceuticals to materials. This book, consisting of an editorial, two reviews and two articles, focuses on recent promising research and novel trends in the field of cross-coupling reactions, employing a range of different catalysts. A review by Kostas and Steele provides a survey of the research in the area of cross-coupling catalytic reactions with transition metal complexes based on the thiosemicarbazone unit and a discussion of the prospects for future developments. Another review by Polychronopoulou, Shaya and co-authors describes the progress made over the 21st century concerning the utilization of C(sp3)–organoboranes as partners in metal-catalyzed C(sp3)–C(sp2) cross-couplings, such as B-alkyl Suzuki–Miyaura reactions. The article by Waldvogel, Breinbauer and co-authors demonstrates for the first time the synthetic potential of combining the electro-oxidative dehydrogenative cross coupling of ortho-substituted phenols with Pd-catalyzed cross-coupling reactions. In the second article, Štĕpnička and co-workers describe the preparation of palladium catalysts deposited over silica gel-bearing composite amide-donor functional moieties on the surface, which were evaluated in the Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes.
Technology: general issues --- Suzuki–Miyaura cross-couplings --- C(sp3) –C(sp2) --- alkylboron reagents --- metal catalysis --- alpha-helix --- anode --- CH-activation --- cross-coupling --- electrosynthesis --- oligoarene --- peptidomimetics --- phenol --- protein-protein interactions --- triflate --- thiosemicarbazone --- metal complex --- transition metal catalysis --- cross-coupling reaction --- Heck reaction --- Suzuki reaction --- Sonogashira reaction --- Kumada reaction --- Buchwald–Hartwig reaction --- deposited catalysts --- palladium --- functional amides --- alkynyl ketone synthesis --- n/a --- Suzuki-Miyaura cross-couplings --- C(sp3) -C(sp2) --- Buchwald-Hartwig reaction
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Transition metal-catalyzed cross-coupling reactions have proved to be powerful tools for carbon–carbon as well as carbon–heteroatom bond formation in the development of synthetic methodologies for applications ranging from pharmaceuticals to materials. This book, consisting of an editorial, two reviews and two articles, focuses on recent promising research and novel trends in the field of cross-coupling reactions, employing a range of different catalysts. A review by Kostas and Steele provides a survey of the research in the area of cross-coupling catalytic reactions with transition metal complexes based on the thiosemicarbazone unit and a discussion of the prospects for future developments. Another review by Polychronopoulou, Shaya and co-authors describes the progress made over the 21st century concerning the utilization of C(sp3)–organoboranes as partners in metal-catalyzed C(sp3)–C(sp2) cross-couplings, such as B-alkyl Suzuki–Miyaura reactions. The article by Waldvogel, Breinbauer and co-authors demonstrates for the first time the synthetic potential of combining the electro-oxidative dehydrogenative cross coupling of ortho-substituted phenols with Pd-catalyzed cross-coupling reactions. In the second article, Štĕpnička and co-workers describe the preparation of palladium catalysts deposited over silica gel-bearing composite amide-donor functional moieties on the surface, which were evaluated in the Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes.
Suzuki–Miyaura cross-couplings --- C(sp3) –C(sp2) --- alkylboron reagents --- metal catalysis --- alpha-helix --- anode --- CH-activation --- cross-coupling --- electrosynthesis --- oligoarene --- peptidomimetics --- phenol --- protein-protein interactions --- triflate --- thiosemicarbazone --- metal complex --- transition metal catalysis --- cross-coupling reaction --- Heck reaction --- Suzuki reaction --- Sonogashira reaction --- Kumada reaction --- Buchwald–Hartwig reaction --- deposited catalysts --- palladium --- functional amides --- alkynyl ketone synthesis --- n/a --- Suzuki-Miyaura cross-couplings --- C(sp3) -C(sp2) --- Buchwald-Hartwig reaction
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The synthesis of enantiopure organic compounds is a key issue for several applications in pharmacology, food chemistry, agricultural chemistry, perfumery, materials science and other industrial sectors. Nowadays, asymmetric catalysis is undoubtedly the most important tool to achieve this goal. This technology, in fact, enables the production of large amounts of enantiomerically enriched compounds, employing relatively small quantities of chiral enantiopure catalysts, which is exactly what is accomplished by enzymes in nature. Since the pioneering works of Noyori, Knowles and Sharpless, which later earned them the Nobel Prize in Chemistry, asymmetric catalysis has experienced a rapid and relentless development in the last fifty years. The tremendous expansion of enantioselective transformations, the design of novel and more efficient organometallic and organic catalysts, the development of sophisticated bioreactors and cell factories, are just some of the elements responsible for such growth. However, new challenges of asymmetric catalysis are devoted to enhancing the process’s sustainability, by the introduction of recyclable and low-cost catalysts, and the use of renewable starting materials and energy source. This book provides an overview of some of these development directions and comprises a collection of review papers and a research article authored by renowned researchers actively involved in this field. The topics covered by the review papers are photoredox-catalyzed reactions of imines, asymmetric catalytic electrosynthesis, cooperative catalysis of chiral N-heterocyclic carbenes and Lewis acid, and asymmetric ring-opening reactions of epoxides catalyzed by metal–salen complexes. The research article presents a proline-catalyzed aldol reaction in water–methanol solvent mixture.
Research & information: general --- N-heterocyclic carbenes (NHC) --- Lewis acid --- cooperative catalysis --- asymmetric synthesis --- umpolung --- amines --- imines --- photoredox catalysis --- radical additions --- radical-radical couplings --- stereoselectivity --- umpolung chemistry --- visible light --- proline --- organocatalysis --- asymmetric aldol reaction --- methanol/water mixtures --- sustainability --- asymmetric catalysis --- salen complexes --- ring-opening --- epoxide --- kinetic resolution --- organic electrosynthesis --- electrochemistry --- enantioselectivity --- transition-metal catalysis --- N-heterocyclic carbenes (NHC) --- Lewis acid --- cooperative catalysis --- asymmetric synthesis --- umpolung --- amines --- imines --- photoredox catalysis --- radical additions --- radical-radical couplings --- stereoselectivity --- umpolung chemistry --- visible light --- proline --- organocatalysis --- asymmetric aldol reaction --- methanol/water mixtures --- sustainability --- asymmetric catalysis --- salen complexes --- ring-opening --- epoxide --- kinetic resolution --- organic electrosynthesis --- electrochemistry --- enantioselectivity --- transition-metal catalysis
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The synthesis of enantiopure organic compounds is a key issue for several applications in pharmacology, food chemistry, agricultural chemistry, perfumery, materials science and other industrial sectors. Nowadays, asymmetric catalysis is undoubtedly the most important tool to achieve this goal. This technology, in fact, enables the production of large amounts of enantiomerically enriched compounds, employing relatively small quantities of chiral enantiopure catalysts, which is exactly what is accomplished by enzymes in nature. Since the pioneering works of Noyori, Knowles and Sharpless, which later earned them the Nobel Prize in Chemistry, asymmetric catalysis has experienced a rapid and relentless development in the last fifty years. The tremendous expansion of enantioselective transformations, the design of novel and more efficient organometallic and organic catalysts, the development of sophisticated bioreactors and cell factories, are just some of the elements responsible for such growth. However, new challenges of asymmetric catalysis are devoted to enhancing the process’s sustainability, by the introduction of recyclable and low-cost catalysts, and the use of renewable starting materials and energy source. This book provides an overview of some of these development directions and comprises a collection of review papers and a research article authored by renowned researchers actively involved in this field. The topics covered by the review papers are photoredox-catalyzed reactions of imines, asymmetric catalytic electrosynthesis, cooperative catalysis of chiral N-heterocyclic carbenes and Lewis acid, and asymmetric ring-opening reactions of epoxides catalyzed by metal–salen complexes. The research article presents a proline-catalyzed aldol reaction in water–methanol solvent mixture.
Research & information: general --- N-heterocyclic carbenes (NHC) --- Lewis acid --- cooperative catalysis --- asymmetric synthesis --- umpolung --- amines --- imines --- photoredox catalysis --- radical additions --- radical–radical couplings --- stereoselectivity --- umpolung chemistry --- visible light --- proline --- organocatalysis --- asymmetric aldol reaction --- methanol/water mixtures --- sustainability --- asymmetric catalysis --- salen complexes --- ring-opening --- epoxide --- kinetic resolution --- organic electrosynthesis --- electrochemistry --- enantioselectivity --- transition-metal catalysis --- n/a --- radical-radical couplings
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The synthesis of enantiopure organic compounds is a key issue for several applications in pharmacology, food chemistry, agricultural chemistry, perfumery, materials science and other industrial sectors. Nowadays, asymmetric catalysis is undoubtedly the most important tool to achieve this goal. This technology, in fact, enables the production of large amounts of enantiomerically enriched compounds, employing relatively small quantities of chiral enantiopure catalysts, which is exactly what is accomplished by enzymes in nature. Since the pioneering works of Noyori, Knowles and Sharpless, which later earned them the Nobel Prize in Chemistry, asymmetric catalysis has experienced a rapid and relentless development in the last fifty years. The tremendous expansion of enantioselective transformations, the design of novel and more efficient organometallic and organic catalysts, the development of sophisticated bioreactors and cell factories, are just some of the elements responsible for such growth. However, new challenges of asymmetric catalysis are devoted to enhancing the process’s sustainability, by the introduction of recyclable and low-cost catalysts, and the use of renewable starting materials and energy source. This book provides an overview of some of these development directions and comprises a collection of review papers and a research article authored by renowned researchers actively involved in this field. The topics covered by the review papers are photoredox-catalyzed reactions of imines, asymmetric catalytic electrosynthesis, cooperative catalysis of chiral N-heterocyclic carbenes and Lewis acid, and asymmetric ring-opening reactions of epoxides catalyzed by metal–salen complexes. The research article presents a proline-catalyzed aldol reaction in water–methanol solvent mixture.
N-heterocyclic carbenes (NHC) --- Lewis acid --- cooperative catalysis --- asymmetric synthesis --- umpolung --- amines --- imines --- photoredox catalysis --- radical additions --- radical–radical couplings --- stereoselectivity --- umpolung chemistry --- visible light --- proline --- organocatalysis --- asymmetric aldol reaction --- methanol/water mixtures --- sustainability --- asymmetric catalysis --- salen complexes --- ring-opening --- epoxide --- kinetic resolution --- organic electrosynthesis --- electrochemistry --- enantioselectivity --- transition-metal catalysis --- n/a --- radical-radical couplings
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This Reprint Book highlights and overviews the most important and novel aspects of chiral auxiliary and chirogenesis in different natural/physical sciences and in modern technologies. In particular, some newly emerging classes of molecules used for these purposes have been described. Furthermore, some important experimental and theoretical issues associated with the chirality field have been addressed. This book consists of one review article and six research papers and is of interest for general chemistry readership, including graduate and post-graduate students, and for researchers specializing in the fields of chirality and stereochemistry
pillar[5]arene --- planar chirality --- chiral resolution --- racemization kinetics --- supramolecular chemistry --- self-induced diastereomeric anisochronism (SIDA) --- enantiomeric analysis --- molecular association --- NMR --- diffusion --- molecular chirality --- self-disproportionation of enantiomers (SDE) --- indole --- asymmetric synthesis --- organocatalysis --- transition-metal catalysis --- C-N bond formation --- enantioselective --- heterocycles --- porphyrinoids --- multinuclear complexes --- chiral ligands --- circular dichroism --- paramagnetic NMR --- magnetochemistry --- porphyrin --- guanidine --- host–guest binding --- chirality --- DFT --- TD-DFT simulation --- induced optical activity --- stereodynamic chirality probe --- exciton coupling --- circularly polarized luminescence --- sergeants-and-soldiers --- majority-rule --- polysilane --- polyfluorenevinylene --- polyfluorene --- mirror symmetry breaking --- parity violation --- n/a --- host-guest binding
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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 --- 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
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This Reprint Book highlights and overviews the most important and novel aspects of chiral auxiliary and chirogenesis in different natural/physical sciences and in modern technologies. In particular, some newly emerging classes of molecules used for these purposes have been described. Furthermore, some important experimental and theoretical issues associated with the chirality field have been addressed. This book consists of one review article and six research papers and is of interest for general chemistry readership, including graduate and post-graduate students, and for researchers specializing in the fields of chirality and stereochemistry
Research & information: general --- pillar[5]arene --- planar chirality --- chiral resolution --- racemization kinetics --- supramolecular chemistry --- self-induced diastereomeric anisochronism (SIDA) --- enantiomeric analysis --- molecular association --- NMR --- diffusion --- molecular chirality --- self-disproportionation of enantiomers (SDE) --- indole --- asymmetric synthesis --- organocatalysis --- transition-metal catalysis --- C-N bond formation --- enantioselective --- heterocycles --- porphyrinoids --- multinuclear complexes --- chiral ligands --- circular dichroism --- paramagnetic NMR --- magnetochemistry --- porphyrin --- guanidine --- host-guest binding --- chirality --- DFT --- TD-DFT simulation --- induced optical activity --- stereodynamic chirality probe --- exciton coupling --- circularly polarized luminescence --- sergeants-and-soldiers --- majority-rule --- polysilane --- polyfluorenevinylene --- polyfluorene --- mirror symmetry breaking --- parity violation --- pillar[5]arene --- planar chirality --- chiral resolution --- racemization kinetics --- supramolecular chemistry --- self-induced diastereomeric anisochronism (SIDA) --- enantiomeric analysis --- molecular association --- NMR --- diffusion --- molecular chirality --- self-disproportionation of enantiomers (SDE) --- indole --- asymmetric synthesis --- organocatalysis --- transition-metal catalysis --- C-N bond formation --- enantioselective --- heterocycles --- porphyrinoids --- multinuclear complexes --- chiral ligands --- circular dichroism --- paramagnetic NMR --- magnetochemistry --- porphyrin --- guanidine --- host-guest binding --- chirality --- DFT --- TD-DFT simulation --- induced optical activity --- stereodynamic chirality probe --- exciton coupling --- circularly polarized luminescence --- sergeants-and-soldiers --- majority-rule --- polysilane --- polyfluorenevinylene --- polyfluorene --- mirror symmetry breaking --- parity violation
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