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| 书名： | Copper-Mediated Cross-Coupling Reactions | |
|---|---|---|
| 作者： | Evano, Gwilherm; Blanchard, Nicolas | |
| 出版时间： | 2013-09-23 | |
| ISBN： | 9781118060452(P-ISBN) ，9781118690680(O-ISBN) | |
| 摘要： | ||
| 摘要： | ||
书目详情：
CoverTitle pageCopyright pageContentsForewordPrefaceContributorsPart I: Formation of C–Heteroatom Bonds1: Modern Ullmann–Goldberg Chemistry: Arylation of N-Nucleophiles with Aryl Halides1.1 Introduction1.2 Arylation of Amines1.3 Arylation of Amides, Imides, and Carbamates1.4 Arylation of Conjugated N-Heterocycles1.5 Synthesis of Anilines by Coupling with Ammonia or Synthetic Equivalents1.6 Conclusion and Future ProspectsReferences2: Ullmann Condensation Today: Arylation of Alcohols and Thiols with Aryl Halides2.1 Introduction2.2 Formation of C–O Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides2.2.1 Coupling of Aryl Halides with Hydroxide Sources: Synthesis of Phenols2.2.2 Coupling of Aryl Halides with Aliphatic Alcohols: Synthesis of Alkyl Aryl Ethers2.2.3 Coupling Reactions of Aryl Halides with Phenols: Synthesis of Biaryl Ethers2.3 Formation of C–S Bonds via Copper-Catalyzed Cross-Coupling Reactions with Aryl Halides2.3.1 Coupling of Aryl Halides with Sulfur Sources: Synthesis of Thiophenols2.3.2 Coupling of Aryl Halides with Aliphatic Thiols: Synthesis of Alkyl Aryl Thioethers or Alkyl Aryl Sulfides)2.3.3 Coupling of Aryl Halides with Aryl Thiols: Synthesis of Diaryl Thioethers or Diaryl Sulfides)2.4 ConclusionReferences3: Copper-Catalyzed Formation of C–P Bonds with Aryl Halides3.1 Introduction3.2 Arylation of Phosphines3.2.1 Arylation of Diarylphosphines3.2.2 Arylation of Dialkylphosphines3.2.3 Application to the Synthesis of Bulky Tertiary Phosphine Ligands3.3 Arylation of Phosphine Oxides and Phosphites3.3.1 Arylation of Phosphine Oxides3.3.2 Synthesis of Aryl Phosphonates by Arylation of Trialkylphosphites and H-Phosphonates3.3.3 Arylation of Other Phosphorus Derivatives3.4 ConclusionReferences4: Alternative and Emerging Reagents for the Arylation of Heteronucleophiles4.1 Introduction4.2 Chan–Lam–Evans Coupling: CopperII)-Promoted Oxidative Aryl Transfer from Arylboron Derivatives4.2.1 Initial Discovery of the Chan–Lam–Evans Coupling4.2.2 Developments in the Oxidative Copper-Mediated Arylation of Heteronucleophiles with Boronic Acids4.2.3 Mechanism of the Coupling4.2.4 Scope4.3 Copper-Promoted Aryl Transfer from Metallated Aryl Derivatives Nonboron)4.3.1 Bismuth and Lead4.3.2 Arylstannanes and Aryl-Alkoxysilanes4.3.3 Aryliodonium Salts4.4 Copper-Catalyzed Arylation Reactions Involving Masked S- and N-Nucleophiles4.4.1 C–S Bond Formation4.4.2 C–N Bond Formation4.5 Copper-Catalyzed Direct Heterofunctionalization of Aromatic C–H Bonds4.5.1 Functionalization of Acidic Aromatic C–H Bonds4.5.2 Directed Aromatic C–H Bonds Functionalization4.5.3 Intramolecular Copper-Catalyzed Heterofunctionalization of Aromatic C–H Bonds4.6 Conclusion and Future ProspectsReferences5: Beyond Ullmann–Goldberg Chemistry: Vinylation, Alkynylation, and Allenylation of Heteronucleophiles5.1 Introduction5.2 Copper-Mediated Alkenylation of Heteronucleophiles: Among the Best Routes to Heteroatom-Substituted Alkenes5.2.1 Synthesis of Enamides, Enamines, and N-Alkenyl-Heterocycles5.2.2 Synthesis of Enol Ethers5.2.3 Synthesis of Vinyl Sulfides and Other Sulfur-Substituted Alkenes5.2.4 Synthesis of Vinylphosphonates and Phosphine Oxides5.3 Alkynylation of Heteronucleophiles: The Emergence of General Methods for the Synthesis of Heteroatom-Substituted Alkynes5.3.1 Bringing Ynamides into the New Millennium: Copper-Mediated Alkynylation of Nitrogen Nucleophiles5.3.2 Copper-Mediated Synthesis of Ynol Ethers: The First Development5.3.3 Copper-Mediated Preparation of Alkynyl Chalcogenides5.3.4 Synthesis of Phosphorus-Substituted Alkynes: The Development of Mild Protocols Based on Copper Catalysis5.4 Allenylation of Heteronucleophiles: New Tools for the Synthesis of Allenamides5.5 Conclusion and Future ProspectsReferences6: Aromatic/Vinylic Finkelstein Reaction6.1 Introduction6.2 Copper-Mediated Halogen Exchange Reactions in Aryl Halides6.2.1 From Early Discoveries to Most Recent Reports6.2.2 Copper-Mediated Fluorination of Haloarenes6.2.3 Mechanistic Investigations in Aryl–CuIII) Model Systems6.3 Most Recent Developments and OverviewReferences7: Insights into the Mechanism of Modern Ullmann–Goldberg Coupling Reactions7.1 General View and Key Mechanistic Aspects7.2 Oxidation State of Copper Catalysts7.3 Identity of the Active CopperI) Complex7.4 Activation Mode of Aryl Halides by Copper Complexes7.4.1 Oxidative Addition/Reductive Elimination Pathway7.4.2 SET Mechanism7.4.3 AT Mechanism7.4.4 Mechanism Involving π-Complexation of CopperI) to Aryl Halides7.4.5 Mechanism Involving σ-Bond Metathesis7.5 Overview, Conclusions, and Future ProspectsReferencesPart II: Formation of C–C Bonds8: Modern Copper-Catalyzed Hurtley Reaction: Efficient C-Arylation of CH-Acid Derivatives8.1 Introduction8.2 Classical Hurtley Reaction8.3 Ligation Effect in Copper-Catalyzed Reactions of Aryl Halides with Carbanions8.4 Cascade Reactions Proceeding via a Hurtley Arylation Reaction8.5 Mechanism of the Copper-Catalyzed C-Arylation Reactions8.6 Concluding RemarksReferences9: Copper-Catalyzed Cyanations of Aryl Halides and Related Compounds9.1 Introduction9.2 Modifications and Updates of Classical Cyanation Reactions Rosenmund–von Braun, Sandmeyer)9.3 Copper-Catalyzed Cyanations of Aryl Halides9.4 Copper-Mediated Oxidative Cyanations9.5 ConclusionReferences10: Copper-Mediated Aryl–Aryl Bond Formation Leading to Biaryls: A Century after the Ullmann Breakthrough10.1 Introduction10.2 Biaryl Synthesis by Coupling of Aryl Halides and Diazonium Salts10.2.1 Ullmann Couplings of Aryl Halides10.2.2 Coupling of Organocopper Reagents Generated from Aryl Halides10.2.3 Coupling of Aryl Diazonium Compounds10.3 Biaryl Synthesis by Coupling of Aryltin, Boron, and Silanes10.3.1 Coupling of Organostannanes10.3.2 Coupling of Organoboranes10.3.3 Coupling of Organosilanes10.4 Biaryl Synthesis by Arylation Involving Arene C–H or C–C Bond Fission10.4.1 Direct C–H Arylation of Arenes with Prefunctionalized Arylating Reagents10.4.2 Direct C–H Arylation with Nonfunctionalized Arylating Agents10.4.3 Decarboxylative Coupling of Benzoic Acid Derivatives10.5 Biaryl Synthesis by Oxidative Coupling of 2-Naphthols10.6 Conclusions and OutlookReferences11: Copper-Catalyzed Alkynylation, Alkenylation, and Allylation Reactions of Aryl Derivatives11.1 Introduction11.2 Copper-Catalyzed Alkynylation of Aryl Derivatives11.2.1 Synthesis of Aryl–Ynes by Stille-Type Cross-Coupling Reaction11.2.2 Synthesis of Aryl–Ynes by Sonogashira-Type Cross-Coupling Reaction11.2.3 Synthesis of Aryl–Ynes by Oxidative Cross Coupling of Alkynes and Arylboronic Acids11.2.4 Synthesis of Aryl–Ynes by Decarboxylative Cross Coupling from Propiolic Acids11.2.5 Synthesis of Aryl–Ynes by Direct C–H Functionalization of Arenes11.3 Copper-Catalyzed Alkenylation of Aryl Derivatives11.3.1 Synthesis of Aryl–Enes by Stille-Type Cross Coupling11.3.2 Synthesis of Aryl–Enes by Suzuki–Miyaura-Type Cross Coupling11.3.3 Synthesis of Aryl–Enes by Heck-Type Cross Coupling11.3.4 Synthesis of Aryl–Enes by Direct C–H Functionalization of Arenes11.3.5 Synthesis of Aryl–Enes by Decarboxylative Cross Coupling11.4 Copper-Catalyzed Strategies for the Formation of Allyl–Aryl Bonds11.5 Conclusion and OutlookReferences12: Copper-Catalyzed Alkynylation and Alkenylation Reactions of Alkynyl Derivatives: New Access to Diynes and Enynes12.1 Introduction12.2 Copper-Catalyzed Synthesis of Symmetrical and Unsymmetrical 1,3-Diynes12.3 Copper-Catalyzed Synthesis of 1,4-Diynes12.4 Synthesis of 1,3-Enynes by Direct Reaction of Vinyl Halides with Alkynes12.5 Synthesis of 1,3-Enynes by Stille-Type Cross-Coupling Reaction12.6 Synthesis of 1,3-Enynes by the Suzuki–Miyaura-Type Cross-Coupling Reaction12.7 Synthesis of 1,4-Enynes by Allylation Reaction of Terminal Alkynes12.8 ConclusionReferences13: Copper-Mediated Alkenylation Reaction of Alkenyl Derivatives: A Straightforward Elaboration of 1,3-Dienes13.1 Introduction13.2 Symmetrical 1,3-Dienes by Homocoupling Reaction of Vinyl Derivatives13.2.1 Coupling of Vinylboranes13.2.2 Coupling of Vinylsilanes13.2.3 Coupling of Vinylstannanes13.2.4 Coupling of Vinyl Halides13.2.5 Miscellaneous13.3 Unsymmetrical 1,3-Dienes by Cross-Coupling Reactions13.3.1 Synthesis of 1,3-Dienes by Stille-Type Coupling13.3.2 Synthesis of 1,3-Dienes by Suzuki-Type Coupling13.3.3 Synthesis of 1,3-Dienes by Heck-Type Coupling13.4 ConclusionsReferences14: Emerging Areas in Copper-Mediated Trifluoromethylations of Aryl Derivatives: Catalytic and Oxidative Cross-Coupling Processes14.1 Introduction14.2 Copper-Catalyzed Trifluoromethylation of Aryl Halides: A Long-Lasting Quest Finally Reached14.3 Copper-Mediated Oxidative Trifluoromethylation Reactions14.4 Conclusion and Future ProspectsReferencesPart III: Applications of Copper-Catalyzed Cross-Coupling Reactions: Heterocycles, Natural Products, Process, and Sustainable Chemistry15: Copper-Mediated Cyclization Reactions: New Entries to Heterocycles15.1 Introduction15.2 Cyclization by C–N Bond Formation15.2.1 Copper-Catalyzed Synthesis of Pyrroloindole Derivatives15.2.2 Copper-Catalyzed Synthesis of Benzimidazole Derivatives15.2.3 Copper-Catalyzed Synthesis of 1,3-Dihydrobenzimidazol-2-One Derivatives15.2.4 Copper-Catalyzed Synthesis of Quinazolines15.2.5 Copper-Catalyzed Synthesis of Quinazolinone Derivatives15.2.6 Copper-Catalyzed Synthesis of 1,2,4-Benzothiadiazine 1,1-Dioxides15.2.7 Copper-Catalyzed Synthesis of 1-Aryl-2-Thioxo-2,3-Dihydroquinazolin-41H)-Ones15.2.8 Copper-Catalyzed Synthesis of Indole Derivatives15.2.9 Copper-Catalyzed Formation of Cyclic Enamides: Efficient Routes to Unsaturated Lactams, Alkylideneazetidines, and Dihydropyrroles15.2.10 Copper-Catalyzed Synthesis of 1,4-Benzoxazines15.3 Cyclization by C–O Bond Formation15.3.1 Copper-Catalyzed Synthesis of Benzoxazole Derivatives15.3.2 Copper-Catalyzed Synthesis of Cyclic Enol and Aryl Ethers15.3.3 Copper-Catalyzed Synthesis of Enol Lactones and Benzopyranones15.4 Cyclization by C–C Bond Formation15.4.1 Copper-Catalyzed Synthesis of Indole Derivatives15.4.2 Copper-Catalyzed Synthesis of 3-Acyloxindoles15.4.3 Copper-Catalyzed Synthesis of Isoquinoline and Isoquinolinone Derivatives15.4.4 Heterocyclic Synthesis Based on a Copper-Catalyzed Sonogashira-Type Cross Coupling15.5 Copper-Catalyzed Double Cross-Coupling Reactions for the Assembly of Heterocycles15.5.1 Synthesis of Benzoxazoles and Oxazoles by Double Copper-Catalyzed Cross Coupling15.5.2 Synthesis of Benzimidazoles by Double Copper-Catalyzed Cross Coupling15.5.3 Synthesis of Benzofurans by Double Copper-Catalyzed Cross Coupling15.5.4 Synthesis of Benzimidazo[1,2-b]isoquinolin-11-one Derivatives by Double Copper-Catalyzed Cross Coupling15.5.5 Synthesis of Pyrrole and Thiophene Derivatives by Double Copper-Catalyzed Cross Coupling15.6 Conclusion and Future ProspectsReferences16: Application of Copper-Mediated C–N Bond Formation in Complex Molecules Synthesis16.1 Introduction16.2 Aryl Amination in Complex Molecule Synthesis16.3 Aryl Amidation in Complex Molecule Synthesis16.4 Arylation of N-Heterocycles in Complex Molecule Synthesis16.5 Vinyl Amidation in Complex Molecule Synthesis16.6 Alkyne Amidation in Complex Molecule Synthesis16.7 Intramolecular C–N Bond Formation in Natural Product Synthesis16.7.1 Copper-Mediated Synthesis of Small- to Medium-Sized N-Heterocycles in Total Synthesis16.7.2 Copper-Mediated Macrocyclization by C–N Bond Formation in Natural Product Synthesis16.8 Summary and OutlookReferences17: Natural Products and C–O/C–S Bond-Forming Reactions: Copper Showed the Way17.1 Introduction17.2 Total Synthesis of Naturally Occurring Diaryl Ethers by Arylation of Phenols17.3 Intramolecular Diaryl Ether Bond-Forming Reactions17.3.1 Macrocyclization17.3.2 Small- to Medium-Sized Oxygenated Heterocycles17.4 Arylation of Alcohols17.5 Vinylation of Alcohols17.6 Copper-Mediated C–S Bond Formation in Natural Product Synthesis17.7 Conclusion and Future ProspectsReferences18: Copper-Catalyzed C–C Bond Formation in Natural Product Synthesis: Elegant and Efficient Solutions to a Key Bond Disconnection18.1 Introduction18.2 Natural Biaryls by Copper-Catalyzed Cross Coupling18.2.1 Classical Ullmann Cross-Coupling Reaction18.2.2 Oxidative Biaryl Coupling of Phenols and Naphthols18.3 Copper-Catalyzed 1,3-Enyne Formation18.4 Copper-Mediated Synthesis of Dienes, Trienes, and Extended Polyenes18.4.1 Copper-Mediated Synthesis of 1,3-Dienes18.4.2 Copper-Mediated Synthesis of 1,3,5-Trienes18.4.3 Copper-Mediated Synthesis of Extended Polyenes18.4.4 Copper Salts as Essential Cocatalysts of Palladium-Catalyzed Stille Cross-Coupling Reactions18.5 Copper-Catalyzed Synthesis of 1,n-Polyynes Natural Products18.5.1 Cadiot–Chodkiewicz Strategies18.5.2 Eglinton Strategies18.5.3 Hay Strategies18.5.4 Copper-Catalyzed Synthesis of Skipped Dienes18.6 Conclusions and Future ProspectsReferences19: Process Chemistry and Copper Catalysis19.1 Introduction and Scope19.2 Copper versus Palladium19.3 Applications19.3.1 Materials Sciences19.3.2 Pharmaceutical Chemistry19.3.3 Crop Science Chemistry19.4 ConclusionReferences20: Reusable Catalysts for Copper-Mediated Cross-Coupling Reactions under Heterogeneous Conditions20.1 Introduction20.2 Copper Nanoparticle-Catalyzed Cross-Coupling Reactions20.2.1 C–C Bond Formation20.2.2 C–N Bond Formation20.2.3 C–S Bond Formation20.2.4 C–O Bond Formation20.2.5 C–Se Bond Formation20.3 Supported Copper-Catalyzed Cross-Coupling Reaction20.3.1 C–C Bond Formation20.3.2 C–X Bond Formation20.4 ConclusionReferencesIndex
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