External photocatalyst-free C-H alkylation of N-sulfonyl ketimines with alkanes under visible light

Chinese Chemical Letters, Год журнала: 2023, Номер 34(9), С. 108509 - 108509

Опубликована: Апрель 28, 2023

Язык: Английский

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Synthesis and site selective C–H functionalization of imidazo-[1,2-a]pyridines

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(36), С. 7267 - 7289

Опубликована: Янв. 1, 2023

Herein we disclose the synthesis and an overview of all functionalization reactions at each carbon atom, viz , C2, C3, C5, C6, C7 C8 imidazo[1,2- a ]pyridine.

Язык: Английский

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Catalytic Asymmetric C–H Activation/Cyclization of Sulfoximines with Sulfoxonium Ylides by a Chiral η⁶-Benzene Ruthenium(II) Catalyst

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 17398 - 17404

Опубликована: Ноя. 12, 2024

Chiral η6-benzene ruthenium(II) (BenRuII)-catalyzed asymmetric C–H activations are challenging and rarely seen in the literature. Herein, activation/cyclization of sulfoximines with sulfoxonium ylides catalyzed by chiral BenRuII catalyst derived from (S)-H8–BINOL is described. It provides efficient access to various sulfur-chiral 1,2-benzothiazine 1-oxides high yields enantioselectivities (up 99% yield 98% ee). Kinetic resolution racemic was also feasible. The reaction mechanism studied tool H/D exchange kinetic isotope effect. metallacycle revealing origin induction prepared, characterized, proved effective for model reaction. This work demonstrates great potential catalysts activation.

Язык: Английский

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LiN(SiMe₃)₂/KO^tBu-Promoted Synthesis of Isoquinolone Derivatives from 2-Methylaryl Aldehydes and Nitriles

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(11), С. 7425 - 7430

Опубликована: Май 17, 2023

A convenient method is proposed for the synthesis of isoquinolone derivatives from 2-methylaryl aldehydes and nitriles through LiN(SiMe3)2/KOtBu-promoted formal [4 + 2] cycloaddition reaction, featuring high atomic economy, good functional group tolerance, easy operation. It enables efficient formation new C-C C-N bonds toward isoquinolones without using preactivated amides.

Язык: Английский

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Cascade C─H‐Alkenylation‐Intramolecular Aminative Cyclization of Benzylsulfonamides for Synthesis of Isoindoline Cores

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

Опубликована: Май 21, 2025

Abstract Several isoindoline‐core‐bearing compounds are pharmaceutically relevant due to their activity against a myriad of diseases. Traditionally, the isoindoline core is synthesized from benzylamines by two‐step synthesis involving ortho ‐C─H alkenylation followed acid‐ or metal‐catalyzed cyclization. In this study, we execute direct one‐step procedure alkenylation‐oxidative intramolecular aminative cyclization pyridinesulfonamide derivatives with different acrylates and vinyl sulfones using Pd(II)‐salt as catalyst, Ag(I)‐salt additive, Cu(II)‐salt oxidant. The reactions tolerant several functional groups on benzylamine well alkyl acrylates, providing products moderate excellent yields. Control experiments computational studies revealed importance pyridine‐3‐sulfonamide for reaction since it provides key site stabilizing an intermediate species which favors C─H activation oxidative amination‐based process.

Язык: Английский

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Photoredox-Cobaloxime Catalysis for Selective Oxidative Dehydrogenative [4+2] Annulation of Imidazo-Fused Heterocycles with Alkenes

Organic Letters, Год журнала: 2024, Номер 26(13), С. 2529 - 2534

Опубликована: Март 21, 2024

A selective oxidative [4+2] annulation of alkenes with imidazo-fused heterocycles has been developed by using the synergistic combination photoredox and cobaloxime catalysts. It allows facile access to various imidazole-fused polyaromatic scaffolds accompanied H2 evolution. This protocol features high regioselectivity as well a broad substrate scope. Detailed mechanistic studies indicate that twice electron/H transfer processes facilitated this catalytic system achieve π-extension alkenes.

Язык: Английский

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CeCl₃-Catalyzed C–H Alkylation of N-Sulfonyl Ketimines with Alkanes and Ether via Photoinduced Ligand-to-Metal Charge Transfer

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(24), С. 18337 - 18343

Опубликована: Дек. 9, 2024

A cerium-catalyzed C–H alkylation of N-sulfonyl ketimines with low-cost and readily available alkanes as alkyl sources was developed. This transformation proceeded through the synergy photoinitiated ligand-to-metal charge transfer (LMCT) using a chlorine radical an HAT reagent air green oxidant. series alkylated were synthesized moderate to good yields in highly atom-economic manner under chemical oxidant-free conditions.

Язык: Английский

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Six-membered ring systems: pyridines and benzo derivatives

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 383 - 425

Опубликована: Янв. 1, 2023

Язык: Английский

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Ru(II)-Catalyzed C(sp²)–H Activation Annulation: Synthesis of Fluorescent Benzoisoquinolonyl Acetate/Peptides from N-Arylamides and Ethyne at Room Temperature

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7485 - 7494

Опубликована: Май 15, 2024

Benzoisoquinolones are aryl ring extended isoquinolinone derivatives, which constituents of alkaloid natural products. This report describes the synthesis novel benzoisoquinolone amino acid/peptide derivatives from respective

Язык: Английский

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