A novel and efficient method for the synthesis of selenophenes is disclosed. Selenophenes were synthesized in high yields in a single operation from 1,3-dienes containing a carbonyl group at the C-1 position and selenium dioxide. The bidirectional synthesis of selenophenes can also be demonstrated using this method. The selenophene is believed to form via a [4 + 2] cycloaddition between diene and selenium dioxide.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo025630t | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Radical-Triggered Bicyclization and Aryl Migration of 1,7-Diynes with Diphenyl Diselenide for the Synthesis of Selenopheno[3,4-]quinolines.
Org Lett
January 2025
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
The translocation of an aryl group from selenium into carbon enabled by the cleavage of the C-Se bond is reported by using nitrogen atom-linked 1,7-diynes and diaryl diselenides as starting materials, leading to various selenophene derivatives in a regioselective manner. This method enables the construction of two C-Se bonds and two C-C bonds through sequential radical bicyclization and 1,2-aryl migration under metal-free conditions. Control experiments and mechanistic studies suggest that this reaction proceeds through the cleavage of the inert C(Ph)-Se bond, facilitating the aryl translocation process.
View Article and Find Full Text PDFExpedient Synthesis of Substituted Thieno[3,2-]thiophenes and Selenopheno[3,2-]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives.
Molecules
November 2024
Hunan Province Key Laboratory for Synthetic Biology of Traditional Chinese Medicine, School of Pharmaceutical Sciences, Hunan University of Medicine, Huaihua 418000, China.
Thieno[3,2-]thiophenes are used as key components in optoelectronic materials, porous hydrogen-storage hosts, organic solar cells, and polymer semiconductors. A step-efficient synthetic protocol was proposed herein for obtaining multisubstituted thieno[3,2-]thiophene and selenopheno[3,2-]selenophenes in moderate to good yields via the bisulfur/biselenium cyclization of alkynyl diols with I/NaSO or selenium. Using this strategy, substitution patterns were obtained for backbone modification in functional materials.
View Article and Find Full Text PDFSelenophene-containing silicon-rhodamine: A novel near-infrared fluorescent probe for Hg detection and its application in cell imaging.
Spectrochim Acta A Mol Biomol Spectrosc
March 2025
Key Laboratory of Industrial Ecology and Environmental Engineering (MOE), School of Environmental Science and Technology, Dalian University of Technology, Dalian 116024, China.
Monitoring of mercury ion (Hg) pollution is one of the eternal themes due to its notorious toxicity. Herein, we elaborately designed a novel fluorescent probe N'-((selenophen-2-yl)methylene)Si-rhodamine B hydrazide (Se-SiRH) by integrating 2-formylselenophene with Si-rhodamine B hydrazide. Se-SiRH exhibited an excellent near-infrared response towards Hg in MeOH/PBS solution (1:1, v/v, pH = 7.
View Article and Find Full Text PDFBarcoding of viable peripheral blood mononuclear cells with selenium and tellurium isotopes for mass cytometry experiments.
Cytometry A
December 2024
Mass Cytometry Core, Lineberger Comprehensive Cancer Center, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina, USA.
Barcoding viable cells combined with pooled sample staining is an effective technique that eliminates batch effects from serial cell staining and facilitates uninterrupted data acquisition. We describe three novel and isotopically pure selenium-containing compounds (SeMals) that are useful cellular labeling tools. The maleimide-functionalized selenophenes (SeMal, SeMal, and SeMal) covalently react with cellular sulfhydryl groups and uniquely label cell samples.
View Article and Find Full Text PDFStructures of a DNA Polymerase Caught while Incorporating Responsive Dual-Functional Nucleotide Probes.
Angew Chem Int Ed Engl
January 2025
Department of Chemistry, Indian Institute of Science Education and Research (IISER), Pune, Dr. Homi Bhabha Road, Pune, 411008, India.
Functionalizing nucleic acids using DNA polymerases is essential in biophysical and biotechnology applications. This study focuses on understanding how DNA polymerases recognize and incorporate nucleotides with diverse chemical modifications, aiming to develop advanced nucleotide probes. We present the crystal structures of ternary complexes of Thermus aquaticus DNA polymerase (KlenTaq) with C5-heterocycle-modified environment-sensitive 2'-deoxyuridine-5'-triphosphate (dUTP) probes.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!