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" Catalytic arylation methods : "
Anthony J. Burke and Carolina Silva Marques
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BL
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594315
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b423534
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Burke, Anthony J., (Anthony Joseph)
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Catalytic arylation methods : : from the academic lab to industrial processes /\ Anthony J. Burke and Carolina Silva Marques
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1 online resource (525 pages) :: illustrations
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9783527672707
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: 3527672702
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: 9783527672745
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: 3527672745
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: 3527335188
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: 9783527335183
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9783527335183
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| Bibliographies/Indexes
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Includes bibliographical references and index
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| Contents
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Cross-Coupling Arylations: Precedents and Rapid Historical Review of the Field -- Metal-Catalyzed Cross-Couplings: From Its Origins to the Nobel Prize and Beyond -- Arylation: What Is So Special? -- Recent New Developments -- Arylations with the Heck-Mizorold Reaction -- Arylations with the Heck-Matsuda Reaction-Recent Developments -- Hiyama-Hatanaka Cross-Coupling Reaction -- Arylations with the Stille Reaction -- Arylations with the Sonogashira-Hagihara Reaction -- Arylations with the Suzuki-Miyaura Reaction -- Tamao-Kumada-Corriu Cross Coupling -- Negishi-Baba Cross-Coupling -- Beyond the Ullmann and Suzuki-Miyaura Reactions, Other Newer Approaches to Functional Biaryl Synthesis: Pd, Fe, Co, and Other Metals -- With Palladium -- With Iron -- With Nickel -- With Cobalt -- Conclusions -- Selected Experiments from tire Literature -- The Heck-Mizoroki Reaction -- Heterogeneous Catalytic Synthesis of (E)-Butyl Cinnamate Using a Palladium Nanosphere Catalyst -- The Preparative Catalytic Synthesis of 5-(p-Trifluoromethylphenyl)-2,3-dihydrofuran in Continuous Flow -- The Heck-Matsuda Reaction -- Catalytic Synthesis of (E)-3-(4-Methoxyphenyl)acrylic acid Using Palladium Acetate in Water -- Catalytic Synthesis of 2-Phenyl-1H-Indene Using Copper Chloride -- Catalytic Synthesis of (E)-Ethyl 3-(4-methoxyphenyl)acrylate Using Palladium Nanoparticles Supported on Agarose Hydrogel -- The Heck - Hiyama Reaction -- Catalytic Synthesis of p-Nitrobiphenyl: Ligand-Free Coupling Using Pd/C -- The Stille Reaction -- The Cu Catalyzed Stille Reaction-Synthesis of AT-Ethyl-N-(phenyl-p-tolylmethyl)benzamide -- The Sonogashira-Hagihara Reaction -- The Copper-Free Catalytic Synthesis of Diphenylethyne -- Sonogashira-Hagihara Cross-Coupling with Arenediazonium Salts-Synthesis of 1-(4-Methoxyphenyl)-2-phenylacetylene -- Tire Suzuki-Miyaura Reaction -- Synthesis of 4-(2,6-Dimetliylphenyl)-3,5-dimethylisoxazole Using Pd-PEPPSI-IPENT -- Synthesis p-Phenylanisole via the Suzuki-Miyaura Reaction with a FibreCat-1034 Catalyst -- Tamao-Kumada-Corriu Cross-Coupling Reaction -- Synthesis of 2-(4-Methoxyphenyi)pyridine -- Negishi-Baba Cross-Coupling -- Synthesis of 1-Mesitylnaphthalene -- Biaryl Synthesis with the Hindered Aryllithium Reagent, 2,6-Dimethoxyphenyllithium: Catalytic Synthesis of l,3-Dimethoxy-2-(l-naphthyl)benzene -- References -- Amine, Phenol, Alcohol, and Thiol Arylation -- Introduction -- Pd-Catalyzed Processes -- Buchwald-Hartwig Arylations (C<sup>Ar<sup>-NR Bond Formation) -- Migita Thioether Synthesis (C<sup>Ar</sup>-SR Bond Formation) -- Arylether Synthesis (C<sup>Ar<sup>-OR Bond Formation) -- Phosphorous Arylations (C<sup>Ar<sup>-P Bond Formation) -- Pd-Catalyzed Phosphorous Arylations (C<sup>Ar<sup>-P Bond Formation) -- Cu-Catalyzed and Promoted Arylations: (C<sup>Ar<sup> - N Bond Formation) -- Arylamines (C-N Bond Formation) -- The Modified Ullmann Reaction (Ullmann-Condensation-Type Arylations) -- Use of Arylboronic Acids and Derivatives Instead of Arylhalides: Chan-Lam-Evans Coupling and Other Variants -- Arylthioethers (C<sup>Ar<sup>-S Bond Formation) -- Use of Arylhalides -- The Chan-Lam-Evans Variant (Use of Arylboronic Acids) -- Arylethers (C<sup>Ar<sup>-O Bond Formation) -- The Cop per-Catalyzed Ullmann Coupling Reaction -- The Chan-Lam-Evans Reaction -- Phosphorous Arylations (C<sup>Ar<sup> -P Bond Formation) -- Fe-Catalyzed Arylations -- Fe-Catalyzed Aryl Animation: (C<sup>Ar<sup>-N Bond Formation) -- Arylethers (C<sup>Ar<sup>-O Bond Formation) -- Arylthioethers (C<sup>Ar<sup>-S Bond Formation) -- Ni-Catalyzed Reactions -- Ni-Catalyzed Amine Arylation: (C<sup>Ar<sup>-N Bond Formation) -- Ni-Catalyzed Sulfide Arylation: (C<sup>Ar<sup>-S Bond Formation) -- Ni-Catalyzed Phosphorous Arylations (C<sup>Ar<sup> -P Bond Formation) -- Co-Catalyzed Arylations -- Co-Catalyzed Amine Arylations: (C<sup>Ar<sup>-N Bond Formation) -- Co-Catalyzed Sulfide Arylation: (C<sup>Ar<sup>-S Bond Formation) -- Mn-Catalyzed Arylations -- Mn-Catalyzed Amine Arylations: (C<sup>Ar</sup>-N Bond Formation) -- Mn-Catalyzed Sulfide Arylation: (C<sup>Ar</sup>-S Bond Formation) -- Cd-Catalyzed Arylations -- Cd-Catalyzed Aryl Amination: (C<sup>Ar</sup>-N Bond Formation) -- Bi(III) and Indium Oxide-Catalyzed Thiol Arylations -- Conclusions and Final Comment -- Selected Experiments from the Literature -- Amine Arylations -- The Buchwald-Hartwig Amine Arylation -- Copper-Catalyzed Amine Arylations -- Fe Arylations -- Thiol Arylation -- Palladium-Catalyzed Arylation -- Copper-Catalyzed Thiol Arylation -- Fe Catalysis -- Etherification Cross-Coupling Reactions -- With Palladium -- With Iron -- References -- Decarboxylase Coupling Techniques -- Introduction -- Pd Catalyzed Versions -- Pd-Based Systems -- Pd/Cu-Based Systems -- Other Metal -Catalyzed Versions -- Cu-Based Systems -- Other Metal -Based Systems -- Conclusions -- Selected Experiments -- Application of Pd Catalysts -- Synthesis of 2-(3-Pyridyl)-1-methylpyrrole -- Synthesis of 1-Methyl-2,3-bis(4-(trifluoromethyl)phenyl)-1H-indole -- Synthesis of 2,6-Dimethoxybiphenyl -- Synthesis of 7-(Diethylamino)-3-(4-methoxyphenyl)-2H-chromen-2-one -- Synthesis of 4-(2-Nitrophenyl)benzophenone -- Synthesis of 3,4'-Dimrthyl-4-nitrobiphenyl -- Synthesis of 4-Methylbenzophenone -- Synthesis of N-[(l-Naphthyl)(phenyl)methylene]cydohexanamine -- Synthesis of 2,3,4, 5,6-Peiitanuoro-2'-niethylbiphenyl -- References -- C- H Bond Activation for Arylations -- Introduction -- C(sp³)-H Activations -- Involving Ar/Ar Couplings C(sp²)-H Activations -- Directed Metalating Group (DMG)-Assisted C(sp²)-H Activations Direct Arylation -- Involving Ar/C=X (X = C, O, N) Couplings C(sp2 )-H Activations -- DMG Ar/C=X (X = C, O, N) Couplings C(sp²)-H Activations -- Non-DMG Ar/OX (X = C, O. N) Couplings C(sp²)-H Activations -- Involving Ar/Alkyne Couplings C(sp²)-H Activations -- DMG Ar/Alkyne Couplings C(sp²)-H Activations -- Non-DMG Ar/Alkyne Couplings C(sp²)-H Activations -- Involving Ar/Alkyl Couplings -- DMG Assisted Ar/Alkyl Couplings C(sp²)-H Activations -- Non-DMG Assisted Ar/Alkyl Couplings C(sp²)-H Activations -- Involving Ar/N Couplings C(sp²)-H Activations -- Involving Ar/Other Heteroatom Couplings -- Conclusions -- Selected Experiments from the Literature -- C<sup>Ar</sup>-H Arylation -- With Palladium -- With Rhodium -- With Ruthenium -- C<sup>Ar</sup>-H C=X (X = C, O, N) Cross-Coupling -- With Rhodium -- With Ruthenium -- C<sup>Ar</sup>-H Alkyne Cross-Couplings -- With Rhodium -- References -- Conjugate Additions -- Conjugate Additions: A Powerful Tool for Appending Organic Residues to Cyclic and Acyclic Substrates -- Applications of Rh Catalysts -- Applications of Pd Catalysts -- Applications of Ru and Other Catalysts -- Ruthenium -- Copper -- Nickel -- Conclusions -- Selected Experiments -- Application of Rh Catalysts -- Synthesis of (S)-3-PheuyIcyclohexanone -- Synthesis of a Bidentate Phosphoramidite Ligand: N.N-Dimethy (R,R)-O-linked phosphoramidite -- Synthesis of (R)-3-(2-Naphthyl)cyclohexanone -- Application of Pd Catalysts -- Synthesis of (-)-2-(Biphenyl-4-yl)-4-oxo-piperidine-l-carboxylic acid tert-Butyl Ester -- Application of Cu Catalysts -- Synthesis of (E)-(+)-3-Ethyl-3-methyleyclohexanone -- References -- Imine Arylations -Synthesis of Arylamines -- Arylation of C=N Bonds: Simple Access to Chiral Amine Units -- Application of Rh Catalysts -- Application of Pd Catalysts -- Application of Ru and Other Catalysts -- Ruthenium -- Zinc -- Copper -- The Petasis-Akritopoulou Reaction -- Conclusions -- Selected Experiments -- Application of Rh Catalysts -- Synthesis of (S)-A/-[(2-Furyl)phenylmethyl]-4-methylbcnzenesulfonamide -- Synthesis of W-(l-(4-Chlorophenyl)-l-phenylpropyl)-tosylamide -- Synthesis of/y-((4-Methoxy-2-metliylphenyl)(phenyl)methyl)-4-s nitrobenzene sulfonamide -- Application of Pd Catalysts -- Synthesis of [(4-Fluorophenyl)phenylmethyl]carbamic acid tert-butyl ester -- Application of Ru and Other Catalysts -- Synthesis of N-[(2-chlorophenyl)(phenyl)methyl]-4-methylbenzenesulfonamide -- Synthesis of Ethyl 2-(4-(dimethylamtno)phenyl)-2 ((methoxycarbonyl)amino) El acetate -- The Petasis-Akritopoulou Reaction -- Synthesis of (±)-AT-(Diphenylm ethyl)-a-phenylglycine -- Synthesis of (R)-2-((4-(Benzyloxy)phenyl)(pyrrolidin-1-yl)methyl)phenoi -- Synthesis of Ethyl 2-phenyl-2-(pyrrolidin-l-yi)acetate -- References -- Carbonyl Group Arylation -- Introduction -- Application of Rh Catalysts -- Additions to
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Aldehydes -- Addition to Ketones -- Application of Pd Catalysts -- Application of Ru and Other Catalysts -- Ruthenium Catalysis -- Nickel Catalysis -- Copper Catalysis -- Platinum Catalysis -- Iron Catalysis -- Zinc Catalysis -- Titanium Catalysis -- Conclusions -- Selected Experiments -- Application of Rh Catalysts -- Synthesis of (R)-(1-Naphthyl)phenylmethanol -- Synthesis of (S)-(2-Chlorophenyl)(mesityl)methanoI -- Synthesis of (E)-Benzo[d] [1,3]dioxol-5-yl(phenyl)methanol -- Synthesis of 1-p-Tolyl-l,2,3,4-tetrahydronaphthalen-l-ol -- Synthesis of (S)-5-Chloro-3-(3,5-dimethylphenyl)-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one -- Application of Pd Catalysts -- Synthesis of 3-Phenyl-3-hydroxy-2,3-dihydrobenzofuran -- Application of Ru Catalysts -- Synthesis of (S)-(4-Chlorophenyl)phenylmethanol -- Application of Cu Catalysts -- Synthesis of (5)-(4-Chlorophenyl)(phenyl)methanol -- Application of Zn Catalysts -- Synthesis of (Cyclonexyl)phenylmemanoI -- Synthesis of (R)-2,2-Dimethyl-l-phenylpropanol -- Synthesis of l-(4'-Methylphenyl)-l-phenylethanol -- References -- α-Arylation Processes -- Introduction -- Arylation of Enolates and Equivalents -- Arylation of Ketones and Aldehydes -- Ketones -- Aldehydes -- Arylation of Amides -- Arylation of Esters -- Other Metal-Catalyzed a-Arylations -- Copper Catalysts -- Nickel Catalysts -- Conclusions -- Selected Experiments -- Arylation of Enolates and Equivalents --
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Synthesis of 2-(4-Biphenyl)-4-methyl-3-pentanone -- Synthesis of α-(o-Tolyl)acetophenone -- Synthesis of 1-Benzyl-4-methyl-1,2,3,4-tetrahydro-4-quinolinoi -- Synthesis of (R)-1,3-Dimethy1-3-phenylindolin-2-one -- Synthesis of tert-Butyl (6-methoxynaphthaien-2-yl) acetate -- Synthesis of tert-Butyl α-mesitylpropanoate -- Other Metal-Catalyzed α-Arylations -- Synthesis of l-Benzyl-6-chloro-5-fluoro-3-(l-hydroxyethylidene)indolin-2-one -- Synthesis of (S)-2-Phenyl-1-octanol -- Synthesis of 2-MethyE2-(4-(trifluoromethyl)phenyl)-2,3-dihydro-1H-inden-1-one -- References -- Catalytic Cycloaddition Aromatization Processes -- Introduction -- Cycloaddition Events -- [2+2+2] Cycloadditions -- With Rhodium -- With Cobalt -- With Ruthenium -- With Palladium -- With Iron -- With Nickel -- With Titanium -- With Iridium -- With Copper -- [3+2]-Cycloadditions for the Synthesis of Aromatic Compounds -- The Huigsen's Reaction -- Tetrazole Synthesis -- Pyrrole Synthesis -- The Diels-Alder Reaction -- Radical-Based Cycloaromatization Processes -- The Catalytic Bergman Cyclization -- The Catalytic Mycrs-Saito Cyclization -- Conclusions -- Selected Experiments from the Literature -- [2+2+2]-Cycloadditton -- Rhodium-Catalyzed Synthesis of 2, 4, 5, 7-Tetraphenylisoindoline -- Cobalt Catalyzed Synthesis of 2-(2-Methoxy-l-naphthyl)-6-phenyl-7,8-dihydro-5H-cyclopenta-Ic]pyridine -- Palladium-Catalyzed Synthesis of an Aromatic Hexa-ester -- Iron-Catalyzed Synthesis of 3,6-Dimethyl-2-n-butyl pyridine -- [3+2]-Cycloaddition: Click-Chemistry -- Cu-Catalyzed Synthesis of 17-[3-(1-(1,2,3-Triazolyl))]estradiol -- Organocatalytic Synthesis of 1,5-Diphenyl-1H-1,2,3-triazole -- Cul-NBS-Mediated Synthesis of N-[5"-(Phenylthio)Phosphorylethoxyethyl]-2',3'-O-isopropylidene-5'-phosphoryl-5-I-l,2,3-triazoIe-4-amide-l-D-ribofuranoside -- Ru-Catalyzed Synthesis of l-Benzyl-5-phenyI-1H-1,2,3-triazoie -- Synthesis of 1-(2-Methylbenzyl)-5-benzoyl tetrazole -- Catalytic Synthesis of Dimethyl 3-Cyclopropyl-1H-pyrrole-2,4-dicarboxylate -- References
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Arylation.
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| Dewey Classification
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541.395
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| LC Classification
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QD341.H9B87 2015eb
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| Added Entry
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Marques, Carolina Silva,1981-
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| Added Entry
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Ohio Library and Information Network.
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