Recent advances in electrochemically enabled construction of indoles DOI
Yu Zheng,

Chunxi Chen,

Yanju Lu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(65), P. 8516 - 8525

Published: Jan. 1, 2024

This review summarizes recent advances in the electrochemically enabled construction of indoles from non-indole-based precursors and their underlying mechanisms.

Language: Английский

Regio- and Stereoselective Synthesis of 3-Selenylazaflavanones and 3-Selenylflavanones via Electrochemically Facilitated Selenylation Cascade DOI

Shaogao Zeng,

Yong Zeng, Hui Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4074 - 4084

Published: Feb. 23, 2024

Herein, an oxidant- and metal-free electrochemical selenylation reaction of chalcones with diselenides for the synthesis 3-selenylazaflavanones 3-selenylflavanones at room temperature was reported. The method proceeded under mild conditions, exhibited a broad substrate scope, provided selenylated products in moderate to excellent yields high regio- stereoselectivity. could also be readily scaled up efficiency. Detailed mechanistic studies through control experiments disclosed that selenium-based radical might participate this transformation.

Language: Английский

Citations

10

Visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions: simple FeBr3 as a dual-functional catalyst DOI
Binbin Huang,

Xinye Tang,

Jiawei Yuan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(30), P. 6198 - 6204

Published: Jan. 1, 2024

Reported herein is a visible-light induced selenocyclization of 2-ethynylanilines under ambient conditions, with simple FeBr 3 as dual-functional catalyst.

Language: Английский

Citations

7

Electrocatalytic Cascade Selenylation/Cyclization/Deamination of 2-Hydroxyaryl Enaminones: Synthesis of 3-Selenylated Chromones under Mild Conditions DOI

Kaili Cen,

Yuan Liu,

Junhong Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8632 - 8640

Published: June 6, 2024

Herein, we disclosed a highly efficient pathway toward 3-selenylated chromone derivatives via electrocatalytic cascade selenylation/cyclization/deamination of 2-hydroxyaryl enaminones with diselenides. This method showed mild conditions, easy operation, wide substrate scope, and good functional group tolerance. Furthermore, this electrosynthesis strategy was amendable to scale-up the reaction. Additionally, preliminary experiments revealed that reaction probably proceeded cation instead radical pathway.

Language: Английский

Citations

6

Electrochemical Synthesis of Organoselenium Compounds: A Graphical Review DOI Creative Commons
Zhixiong Ruan,

Balati Hasimujiang

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 511 - 520

Published: Oct. 1, 2023

Abstract Electrochemical synthesis, due to its environmentally benign, sustainable, and practical nature, has become an appealing powerful substitute for traditional methods oxidizing reducing organic compounds. Thus, numerous valuable changes have been established in the field of synthesis through utilization electrochemistry. Among these electrochemical transformations, formation C–Se bonds stands out as exceptionally noteworthy reaction type. In this graphical review, we present a succinct summary progress utilizing strategies synthesizing organoselenium

Language: Английский

Citations

12

Modular Synthesis of Bioactive Selenoheterocycles for Efficient Cancer Therapy via Electrochemical Selenylation/Cyclization DOI
Wenyan Xu,

Chengwei Zheng,

Mu Chen

et al.

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

Published: March 10, 2025

A green, efficient, and environmentally friendly electrochemical strategy was developed for synthesizing a series of selenoheterocyclic compounds. The antitumor activities these compounds were evaluated, revealing that 4o, 5n, 5o demonstrated remarkable efficacy. These effectively inhibited lung cancer by inducing cell apoptosis, causing DNA damage, suppressing the progression epithelial-mesenchymal transition. Notably, compound identified as first inhibitor DEAD-box helicase 10 (DDX10). An in vivo xenograft assay further confirmed therapeutic potential 5o, demonstrating tumor growth inhibition rates 60%, 78%, 88% at doses 5 mg/kg, 20 respectively. This study highlights promising chemotherapeutic agent effective treatment cancer.

Language: Английский

Citations

0

Synthesis of organoselenium compounds using electrochemical and photochemical methods as novel approaches in organic chemistry DOI
Adrián A. Heredia, Lydia M. Bouchet, Willber D. Castro‐Godoy

et al.

Tetrahedron, Journal Year: 2023, Volume and Issue: 148, P. 133667 - 133667

Published: Sept. 26, 2023

Language: Английский

Citations

5

Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides DOI Open Access
Jinhui Cai,

Kaili Cen,

Weishuang Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 19, 2024

Abstract Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization ynamides was disclosed. A series diaryl diselenides, dialkyl and heteroaryl‐substituted tolerated in this protocol delivered 4‐selenyloxazolones 28–83% yields. The scale‐up reaction the oxidation performed to showcase practicability method. Furthermore, mechanistic experiments indicated that a cationic pathway instead radical probably involved.

Language: Английский

Citations

1

Recent Developments in Selenylation of Alkynes DOI

Yuemei Xu,

Dayun Huang,

Jinjing Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 29, 2024

Abstract Alkynes are simple yet important organic feedstocks. The selenylation of alkynes is able to produce complex selenium‐containing compounds in a facile way. Although there some reviews about the alkynes, most them focus on one specific reaction or what types products that can be obtained. There lack attention given various uses different selenium reagents and their mechanisms. This review mainly focuses recent advances (2013–2023) based diverse reagents. Mechanisms how added work will discussed. Different types, including difunctionalization, Se‐annulation, spiro‐cyclization, C−Se coupling, click recorded this review. regioselectivity achieved through mechanisms, radicals, seleniraniums electrophilic cyclization. We hope it do help for future research area.

Language: Английский

Citations

1

Electrochemical Oxidative Cross-Coupling and Annulation for Functionalized Heterocycles DOI
Xinwei Hu, Zhixiong Ruan

Topics in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 37 - 53

Published: Jan. 1, 2024

Language: Английский

Citations

0

Recent advances in electrochemically enabled construction of indoles DOI
Yu Zheng,

Chunxi Chen,

Yanju Lu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(65), P. 8516 - 8525

Published: Jan. 1, 2024

This review summarizes recent advances in the electrochemically enabled construction of indoles from non-indole-based precursors and their underlying mechanisms.

Language: Английский

Citations

0