A Practical and Regioselective Strategy for Aromatic C–H Difunctionalization via Site-Selective C–H Thianthrenation

Organic Letters, Год журнала: 2024, Номер 26(9), С. 1813 - 1818

Опубликована: Фев. 22, 2024

Herein, we present a novel Catellani-type reaction that employed aryl-thianthrenium salts as aryl substrates to trigger the subsequent palladium/norbornene cooperatively catalyzed progress. This strategy can achieve site-selective C–H difunctionalization of compounds without directing groups or known initiating reagent. A series functionalized syntheses bioactive molecules further demonstrated potential this strategy.

Язык: Английский

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Diverse Ipso Arene Functionalization by the Palladium/Norbornene Cooperative Catalysis

Опубликована: Фев. 28, 2025

Язык: Английский

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Pd/NBE-Catalyzed One-Pot Modular Synthesis of Tetrahydro-γ-carbolines

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

Опубликована: Апрель 14, 2025

Tetrahydro-γ-carbolines are especially outstanding fused heterocyclic ring systems possessing significant biological activities in the central nervous system. Here, using commercially available NBE derivatives (NBEs), we report an efficient protocol for one-pot modular synthesis of 4-substituted tetrahydro-γ-carbolines via Catellani/aza-Michael addition cascade from easily 3-iodo-1-tosyl-1H-indole, aziridines and olefins. This approach exhibits a wide substrate scope, good yields, scalability, potential extension toward Mebhydroline analogues.

Язык: Английский

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Lewis Acid-Catalyzed Formal [4 + 2] Reaction of Alkynyl Sulfides and 2-Pyrones To Access Polysubstituted Aryl Sulfides

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 7280 - 7285

Опубликована: Май 8, 2024

A practical and efficient method to access polysubstituted aryl sulfides has been discovered via a Lewis acid-catalyzed reaction between alkynyl sulfide 2-pyrone, involving Diels-Alder/retro-Diels-Alder pathway. Alkynyl as an electron-rich dienophile 2-pyrones electron-poor dienes are conjunctively transformed into series of with broad functional group compatibility in good excellent yields (40 examples, 43-88% yield). The robustness practicality the protocol demonstrated through gram-scale synthesis ease transformation resulting products.

Язык: Английский

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Direct Synthesis of C4-Acyl Indoles via C–H Acylation

Organic Letters, Год журнала: 2024, Номер 26(23), С. 4998 - 5003

Опубликована: Июнь 5, 2024

The direct synthesis of C4-acyl indoles deprived C2 and C3 substituents has proven to be challenging, with scarce efficient synthetic routes being reported. Herein, we disclose a highly site-selective palladium-catalyzed C-H acylation for the construction via Catellani-Lautens cyclization strategy. In addition, systematically studied

Язык: Английский

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Palladium/norbornene/copper-catalysed intermolecular thio-esterification from ketones: modular access towards tetrasubstituted vinyl sulfides

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(24), С. 6185 - 6191

Опубликована: Янв. 1, 2023

A Catellani-type α-alkoxycarbonylation/ ipso -thiolation of enol triflates from ketones to access diverse tetrasubstituted vinyl sulfides has been developed.

Язык: Английский

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