Self-catalytic photochemical three-component reaction for the synthesis of multifunctional 3,3-disubstituted oxindoles

Molecular Catalysis, Год журнала: 2024, Номер 565, С. 114379 - 114379

Опубликована: Июль 9, 2024

Язык: Английский

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Brønsted Acid‐Catalyzed Enantioselective and para‐Selective Addition of Phenols to 1‐Alkynylnaphth‐2‐ols

Advanced Synthesis & Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Янв. 22, 2025

Abstract A chiral Brønsted acid‐catalyzed synthesis of axially alkenes was developed via an enantioselective and para ‐selective Friedel–Crafts reaction between phenols 1‐alkynylnaphth‐2‐ols. This methodology features efficient hydroarylation with high functional group tolerance, complete ‐selectivity, excellent yields (up to 99%), enantioselectivities 94% ee) in the presence a N ‐triflylphosphoramide catalyst. DFT calculations were performed investigate ‐selectivity results indicate that both kinetics thermodynamics parameters are more favorable compared ortho ‐selectivity.

Язык: Английский

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Pd-Catalyzed Asymmetric Synthesis of Chiral 2-Trifluoromethyl-4-(indol-3-yl)-4H-chromene Derivatives

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 29, 2025

This paper presents a new strategy for the construction of chiral 4H-chromene skeleton. A series 2-trifluoromethyl-4-(indol-3-yl)-4H-chromenes were synthesized in moderate to good yields (60-92%) with excellent enantioselectivity (up 97% ee) through palladium-catalyzed asymmetric condensation 2H-chromenes and indoles. These trifluoromethylated, stereochemically rich building blocks hold potential value medicinal chemistry.

Язык: Английский

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Halogen Bonding Promoted Photoinduced Synthesis of 3,3-Disubstituted Oxindoles

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 24, 2025

A photoinduced and catalyst-free radical cyclization process for the synthesis of 3,3-disubstituted oxindoles is reported. This method utilizes readily available α-bromoanilides as substrates, showcasing a broad substrate scope. The reaction mechanism facilitated by photoactivated charge transfer complex based on halogen bonding α-bromoanilide with TMG alcohol.

Язык: Английский

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Cu(II)‐Catalyzed Enantioselective Aza‐Friedel‐Crafts Reaction of 1‐Naphthols and Electron‐Rich Phenols with Isatin‐Derived Ketimines

Chemistry - A European Journal, Год журнала: 2024, Номер 30(27)

Опубликована: Март 4, 2024

New chiral ligands could be obtained by introducing proline moieties and imidazoline to binaphthyl skeletons. The exhibited balanced rigidity flexibility which allow the change of conformations during reactions on one hand, provide sufficient asymmetric induction other. moiety act as a linker connecting skeletons well coordinating group for central metal, electronic steric properties groups carefully fine-tuned use different substituents. In presence Cu(II) catalyst bearing such ligands, aza-Friedel-Crafts reaction 1-naphthols electron-rich phenols with isatin-derived ketimines provided desired products good excellent yields up 99 % ee. showed scalability, ee still when was carried out in gram-scale.

Язык: Английский

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Reversal of enantioselectivity by tuning the ring size of ProPhenol

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4109 - 4118

Опубликована: Янв. 1, 2024

Reported herein is the ligand-ring-size controlled enantiodivergent aza-Friedel–Crafts alkylation reaction of 3-aminophenols with imines.

Язык: Английский

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Enantioselective aza-Friedel–Crafts alkylation of aniline derivatives with cyclic N-sulfonyl α-ketiminoesters: the effect of catalyst confinement and the rationale behind the high enantioselectivity

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(19), С. 5462 - 5472

Опубликована: Янв. 1, 2024

In the presence of structurally confined chiral catalysts, mechanism reaction could be altered and aromatization intermediates became key factor governing high enantioselectivity reactions.

Язык: Английский

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Construction of Contiguous Quaternary Carbon Centers Enabled by Dearomatization of Phenols with 3-Bromooxindoles

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Dearomatization of phenols through conjugate addition to in situ generated indol-2-one from 3-bromooxindole construct 3-substituted oxindoles containing contiguous quaternary carbon centers is presented.

Язык: Английский

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Asymmetric Synthesis of Polycyclic Heterocyclic Compounds via Friedel–Crafts Reaction/Cyclization Reaction Catalyzed by Nickel Catalyst

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9877 - 9884

Опубликована: Ноя. 11, 2024

The first highly enantioselective asymmetric Friedel-Crafts reaction/cyclization reaction of 5-aminopyrazoles with 3-alkenyloxindoles to afford polycyclic heterocyclic compounds bearing an all-carbon quaternary stereocenter catalyzed by a complex Ni

Язык: Английский

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