Electrochemical [3+3] Annulation of Phenol and Hydrazone: Synthesis of 1,3,4-Oxadiazines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 19, 2025

A novel [3+3] cyclization reaction between phenol and hydrazone was successfully developed under electrochemically driven conditions. This provided access to a diverse array of 1,3,4-oxadiazinane compounds in consistently high yields, reaching up 87%. Notably, the exhibited remarkable tolerance toward broad spectrum both substrates, underscoring its versatility. Moreover, protocol distinguished itself by exceptional atom step economy, facilitating efficient construction functionalized 1,3,4-oxadiazines. The synthetic utility this approach further exemplified scalability, as demonstrated gram-scale reactions, substrate scope.

Language: Английский

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Single-electron transfer enables enantioselective synthesis of spirooxindoles via dual copper and phosphoric acid catalysis

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111250 - 111250

Published: April 1, 2025

Language: Английский

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Cyclization Through Dual C(sp³)−H Functionalization

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3542 - 3563

Published: July 11, 2024

Abstract C( sp 3 )−H functionalization methods have been widely employed in many organic transformations such as cyclization reactions, heterocycle synthesis, cross‐coupling protocols, and photochemical transformations. Among these transformations, reaction through offers a direct route to convert simple linear substrates complex products. There are three common modes of utilizing bonds reactions including single, double, dual functionalization. As the most challenging mode, refers converting two separate one molecule into desired C−Z which can be reactions. Cyclization via classified based on C−H reactivities. Therefore, categorized classes types activated‐activated, activated‐unactivated, unactivated‐unactivated bonds. Most published reports for involve activated‐activated However, number reported papers other has growing. This review focuses protocols used categorizes

Language: Английский

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Copper‐Catalyzed Tunable Oxygenative Rearrangement of Tetrahydrocarbazoles

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: June 3, 2024

Herein, we report a general copper-catalyzed method for the tunable oxygenative rearrangement of tetrahydrocarbazoles to cyclopentyl-bearing spiroindolin-2-ones and spiroindolin-3-ones. The demonstrates excellent chemoselectivity, regioselectivity, product control simply by using H

Language: Английский

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Direct Synthesis of N-Fused Indoles Enabled by Copper-Catalyzed Aerobic Oxygenative Rearrangement

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(22)

Published: Nov. 4, 2024

N-Fused indoles are typical N-heterocycles, which extensively found in natural products and bioactive molecules. Despite their importance, the synthesis of N-fused has not yet been fully developed. Herein, we report a direct, general unified copper-catalyzed aerobic oxygenative skeletal rearrangement strategy using readily available cyclic indole substrates, provides practical synthetic platform for rapid construction wide array scaffolds. This open-flask method features mild reaction conditions, high chemoselectivity, broad substrate scope (over 90 examples). The scaled-up versatile transformations various nucleophiles demonstrated scalability utility this protocol. Mechanistic studies revealed that, by involving unique single-electron transfer (SET)-induced oxygenation mechanism, tetrahydro-γ-carbolines proceeded via formal 1,3-migration rearrangement, while that tetrahydrocarbazoles Witkop–Winterfeldt/C–C cleavage cascade.

Language: Английский

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Regio- and Stereoselective Construction of 1,3,5-Triaroylcyclohexanes via KO^tBu-Mediated Cyclotrimerization of Aryl Vinyl Ketones

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Herein, we disclose a simple one-pot method for an efficient regio- and stereoselective synthesis of 1,3,5-triaroylcyclohexanes from aryl vinyl ketones using potassium

Language: Английский

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