Visible-light-promoted cascade selenylative cyclization of 2-alkynylthioanisoles for the synthesis of seleno-benzothiophenes DOI
Zhanghong Wang, Jiale Li, Shupeng Zhang

et al.

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 549, P. 113469 - 113469

Published: Aug. 25, 2023

Language: Английский

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

Dilshat Abdukerem,

Hui Chen,

Zechuan Mao

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(10), P. 2075 - 2080

Published: Jan. 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.

Language: Английский

Citations

4
FeCl3-Catalyzed Oxidative Diselenylation of Pyrrole-tethered Indoles DOI
Jing Zhou,

Xue Sheng,

Man Jiang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 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%).

Language: Английский

Citations

0
Photocatalyzed Annulation‐Biselenylation of Enynone with Diarylselenides toward Biselenium‐Substituted 1‐Indanones under Metal‐ and Photosensitizer‐Free Conditions DOI
Hang‐Dong Zuo,

Huafeng Yan,

Yuting Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 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%.

Language: Английский

Citations

0
Radical annulation of a designed diene system: access to nitro-benzo[b]azepines DOI
Kai Sun, Yan Zhang, Miao Tian

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(69), P. 9658 - 9661

Published: Jan. 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.

Language: Английский

Citations

14
Ring-Opening Selenation of Cyclopropanol for the Selective Synthesis of β-Hydroxy-Substituted Selenylated Ketones DOI
Jun Yao, Dandan Hu, Jun‐Qi Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14685 - 14694

Published: Oct. 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.

Language: Английский

Citations

12
Photo/Electrochemical‐Mediated C(sp3)−H Bond Functionalization of (Thio)Ethers DOI

Lianglong Sun,

Dongyang Zhao, Kai Sun

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(17)

Published: March 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.

Language: Английский

Citations

2
Electro-Oxidative C3-Selenylation of Pyrido[1,2-a]pyrimidin-4-ones DOI Creative Commons
Jianwei Shi,

Zhichuan Wang,

Xiaoxu Teng

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(5), P. 2206 - 2206

Published: Feb. 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.

Language: Английский

Citations

6
Synthesis of 3(2H)-furanone derivatives: p-TsOH/halotrimethylsilane promoted cycloketonization of γ-hydroxyl ynones DOI
Yi‐Feng Qiu,

Jian-He Cao,

Shutao Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(43), P. 8744 - 8748

Published: Jan. 1, 2023

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

Language: Английский

Citations

6
Palladium‐Catalyzed Remote δ‐C−H Selenylation of Arylethylamide and Alkenylethylamide Derivatives DOI
Wenbo Ma, Yunhao Zhou, Yang Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(20), P. 3544 - 3550

Published: Sept. 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

Language: Английский

Citations

9
Copper(I)-Catalyzed Three-Component Selenosulfonation of Maleimides with Sulfonyl Hydrazides and Diselenides via Radical Relay DOI

Hong‐Li Ruan,

Yunxia Deng, Zijing Li

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(22), P. 15661 - 15669

Published: Nov. 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.

Language: Английский

Citations

9