Transition metal-free C(sp³)–H selenation of β-ketosulfones

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(10), С. 2075 - 2080

Опубликована: Янв. 1, 2024

Direct C(sp 3 )-H selenation, which is most atom economical, remains a formidable challenge, and only few examples have been reported to date. In this article, we introduce the transition metal-free selenation with β-ketosulfones diselenides as material source.

Язык: Английский

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FeCl3-Catalyzed Oxidative Diselenylation of Pyrrole-tethered Indoles

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A mild and efficient FeCl 3 -catalyzed oxidative diselenylation of pyrrole-tethered indoles has been achieved by using RSeSeR as the source selenium m -chloroperoxybenzoic acid ( CPBA) oxidant (yields 17–70%).

Язык: Английский

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Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 17, 2025

Comprehensive Summary A practical photocatalytic annulation‐biselenylation strategy has been developed for the efficient synthesis of biselenium‐substituted 1‐indanones (38 examples in total) with generally good yields (up to 95%) and excellent stereoselectivity (>19 : 1 Z / E ratio) by employing enynones diaryl selenides as starting materials under photosensitizer‐free conditions. The reaction mechanism involves a cascade process comprising homolytic cleavage, radical addition, 5‐ exo ‐ dig cyclization, capture, enabling sequential formation multiple bonds, such C(sp 3 )‐Se, )‐C(sp 2 ), )‐Se rapidly construct molecular complexity. Notably, this approach demonstrates wide substrate compatibility tolerability towards various functional groups. It is further characterized its remarkable efficiency creating chemical bonds achieving high atomic utilization 100%.

Язык: Английский

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Radical annulation of a designed diene system: access to nitro-benzo[b]azepines

Chemical Communications, Год журнала: 2022, Номер 58(69), С. 9658 - 9661

Опубликована: Янв. 1, 2022

Herein, we describe a novel O2N˙-triggered ordered addition 7-endo cyclization reaction with excellent chemo- and regioselectivity. With such strategy, structurally diverse nitro-benzo[b]azepines were prepared 28 examples. Large-scale operation handy N-Ts N-Cbz deprotection reveal the promising utility of this methodology. Mechanistic studies suggest that proceeds through radical pathway.

Язык: Английский

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Ring-Opening Selenation of Cyclopropanol for the Selective Synthesis of β-Hydroxy-Substituted Selenylated Ketones

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(21), С. 14685 - 14694

Опубликована: Окт. 7, 2022

Ring opening of cycloalkanols has been employed as a commonly used strategy to prepare diverse distal functionalized ketones. However, most these ketones obtained by this belong monofunctional ketones, while difunctional with more potential application value have rarely reported. Herein, we first reported mild I2-promoted ring-opening selenation cyclopropanol synthesize various In the reaction, hydroxyl (−OH) derived from water and RSe+ diselenide can be introduced into α- β-positions, respectively, delivering β-hydroxy selenylated in good excellent yields.

Язык: Английский

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Photo/Electrochemical‐Mediated C(sp³)−H Bond Functionalization of (Thio)Ethers

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(17)

Опубликована: Март 11, 2024

Abstract Molecules containing ether skeletons are widely present in drugs, natural products, functional materials, and life science. Direct C(sp 3 )−H bond functionalization is considered a powerful strategy for the construction of novel derivatives. Photo‐/electro‐chemical technology relatively green sustainable synthesis method, which opens up broad application prospect field direct bonds. In recent years, photo‐/electro‐mediated alkylation, arylation, alkynylation, esterification, mercaptoylation, sulfidation, amination ethers have been extensively studied. this review, research progress compounds from 2014 to 2023 systematically reviewed, scope, limitations, mechanisms some reactions discussed.

Язык: Английский

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Electro-Oxidative C3-Selenylation of Pyrido[1,2-a]pyrimidin-4-ones

Molecules, Год журнала: 2023, Номер 28(5), С. 2206 - 2206

Опубликована: Фев. 27, 2023

In this work, we achieved a C3-selenylation of pyrido[1,2-a]pyrimidin-4-ones using an electrochemically driven external oxidant-free strategy. Various structurally diverse seleno-substituted N-heterocycles were obtained in moderate to excellent yields. Through radical trapping experiments, GC-MS analysis and cyclic voltammetry study, plausible mechanism for selenylation was proposed.

Язык: Английский

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Synthesis of 3(2H)-furanone derivatives: p-TsOH/halotrimethylsilane promoted cycloketonization of γ-hydroxyl ynones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(43), С. 8744 - 8748

Опубликована: Янв. 1, 2023

A halotrimethylsilane facilitated cycloketonization of γ -hydroxyl ynones is detailed for one-step synthesis polysubstituted 3(2 H )-furanone products.

Язык: Английский

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Palladium‐Catalyzed Remote δ‐C−H Selenylation of Arylethylamide and Alkenylethylamide Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(20), С. 3544 - 3550

Опубликована: Сен. 2, 2022

Abstract A palladium‐catalyzed remote δ ‐C−H selenylation of arylethylamide derivatives with readily available diselenides has been reported. This protocol relies on the use a removable picolinamide directing group to access unsymmetrical diaryl selenides in 45–98% yields. Furthermore, inactivated ‐C(alkenyl)−H bond was also compatible this reaction and afforded thermo‐dynamically unfavorable Z ‐selective‐alkenyl complete control site‐ stereoselectivity. magnified image

Язык: Английский

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Copper(I)-Catalyzed Three-Component Selenosulfonation of Maleimides with Sulfonyl Hydrazides and Diselenides via Radical Relay

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(22), С. 15661 - 15669

Опубликована: Ноя. 1, 2022

By employing Cu(CH3CN)4PF6 as the catalyst and tert-butyl hydroperoxide oxidant, we realized a three-component radical selenosulfonation of substituted maleimides, sulfonyl hydrazides, diphenyl diselenides, providing series 3,4-selenosulfonylated succinimides in moderate to good yields. This reaction features broad substrate scopes, high functional-group tolerability, feasibility gram-scale synthesis, enabling one-step construction C–SO2 C–Se bonds under mild conditions. Preliminary mechanistic studies support free-radical-induced pathway.

Язык: Английский

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