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Copper‐Catalyzed Decarbonylative Cyclization of Isatins and Trifluoroacetimidohydrazides for the Synthesis of 2‐(5‐Trifluoromethyl‐1,2,4‐triazol‐3‐yl)anilines

A copper-catalyzed intramolecular decarbonylative cyclization reaction of isatins and trifluoroacetimidohydrazides for the synthesis of 2-(5-trifluoromethyl-1,2,4-triazol-3-yl)aniline derivatives has been developed. This transformation proceeds through a cascade condensation, hydrolysis, decarboxylation and intramolecular C-N bond formation sequence....

Diels‐Alder Cycloaddition of Azepino[4,5‐b]indoles Towards Hydrocarbazole Derivatives and Related Heterocycles

Abstract An approach to hydrocarbazoles bearing an all-carbon quaternary center at C4a position was developed via a Brønsted acid-initiated Diels-Alder cycloaddition/retro-aza-Michael addition cascade process from azepino[4,5-b]indoles and commercially available dienophiles. The method provided a range of hydrocarbazoles in 63–99% yields. The practicality...

Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition

Abstract Electrochemical synthesis of cyclic ether-annulated tetrahydroquinolines from imines and cyclic ethers in an undivided cell under constant current conditions was developed. The electrosynthesis proceeds via the enol ether formation from ethers following the aza-Diels-Alder [4+2] cycloaddition. The method is applicable to a wide range of imines...

Flexible Construction of Functionalized‐Pyrroles under Palladium or Copper Catalysis in the Presence of BF3 ⋅ Et2O

Abstract We have developed a flexible approach enabling the access to highly functionalized pyrroles under palladium or copper catalysis in the presence of BF3 ⋅ Et2O. This catalytic methodology utilizes commercially available amines as reaction partners, and features ample scope, scalable and friendly operations with the generation of only water as...

Palladium‐Catalyzed Stereoselective Intramolecular Heck Dearomative Silylation of Indoles

Abstract A palladium-catalyzed stereoselective intramolecular Heck dearomative of indoles with silyl termination has been developed. A type of tetracyclic indoline derivatives containing silicon were prepared, involving N-(2-bromobenzoyl)indoles and silylboronates. This protocol not only led to a broad substrate scope in acceptable yields but also...

Cross‐Electrophile Coupling between Aryl/Vinyl Triflates and Vinyl Tosylates for the Synthesis of gem‐Difluoroalkenes via Ni/Pd Cooperative Catalysis

A dual nickel-/palladium-catalyzed direct gem-difluorovinylation of readily available aryl/vinyl triflates with substituted gem-difluorovinyl tosylates is presented. This protocol affords various diaryldifluoroalkene, arylalkyldifluoroalkene and 1,1-difluoro-2-substituted-1,3-dienes under mild reaction conditions with excellent functional group compatibility,...

Palladium‐Catalyzed Alkynylation of Alkenes via C‐H Activation for the Preparation of Conjugated 1,3‐Enynes

A general palladium-catalyzed method for the direct alkynylation of unactivated alkenes via C-H activation, was successfully developed, with the assistance of 8-aminoquinoline. It is applicable to both internal and terminal unactivated alkenes with a broad functionality tolerance. This method shows good regio- and stereoselectivity and provides an alternative...

Palladium‐Catalyzed Monofluoroalkylation of Aryl Iodides and Aryl Bromides with Nucleophilic Ethyl 2‐Fluoro‐2‐(trimethylsilyl)acetate

A palladium-catalyzed cross-coupling reaction of aryl iodides and aryl bromides was developed using nucleophilic ethyl 2-fluoro-2-(trimethylsilyl)acetate as a monofluoroalkyl source. The transformation proceeded with excellent substrate scope to afford a range of monofluoroalkylated products in good yields under mild conditions, and it proved feasible...

Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone

A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a wide range of functional group. The study of UV-Vis spectrum indicated that hydrazone and its complex...

Single‐Operation Decarboxylative Mannich Reaction/Asymmetric Transfer Hydrogenation Cascade Process Directly Accesses 1,3‐Distereocentered β‐Sulfonamido Alcohols

The development of cooperative catalysis is of great significance for multi-step sequential enantioselective organic transformations. However, the complicated subtle environments and inherent mutual deactivations of chiral dual catalysts pose a great challenge in a single operation. To address these issues, we here report the rational design of an integrated...

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