A transition metal-free one-pot, three-steps protocol combining N-alkynylindoles, n-butyllithium, elemental selenium, and an electrophile source was developed to allow the synthesis of 3-(organoselanyl) selenazolo indoles. Substrate scope was studied by varying the structure of N-alkynylindoles and the electrophile source. This sequential reaction proceeded selectively through an initial intramolecular 5- endo-dig mode with two new carbon-selenium bonds formation in a one-pot procedure. The reaction conditions were also compatible with elemental sulfur and tellurium, which led to construct 3-(alkylthio) thiazolo indoles and 3-(alkyltelluro) tellurazolo indoles, respectively. In addition, it was also demonstrated that a series of dichalcogenides derived from chalcogenazoloindoles ring could be easily prepared via oxidation of chalcogenolate anion in contact with air.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.9b00052 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of 1,4-Diketones from Esters Enabled by a Tetraborylethane Reagent.
Org Lett
January 2025
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu 730000, China.
A modular synthesis method for 1,4-diketones has been developed. Utilizing inexpensive carboxylic acid esters as carbonyl sources and tetraborylethane () as a nucleophilic reagent, a one-pot strategy for constructing two C-C bonds was established. Notably, this reaction proceeds without the involvement of transition metals and exhibits excellent functional group compatibility.
View Article and Find Full Text PDFLight-dependent Br-org production in terrestrial plants under acetaminophen stress and the bromination mechanisms mediated by photosystem.
J Environ Sci (China)
July 2025
School of Environmental Science and Engineering, Shandong Key Laboratory of Environmental Processes and Health, Shandong University, Qingdao 266237, China; Laboratory of Marine Ecological Environment in Universities of Shandong, Shandong University, Qingdao 266237, China; Qingdao Key Laboratory of Marine Pollutant Prevention, Shandong University, Qingdao 266237, China; Shandong Kenli Petrochemical Group Co., Ltd., Dongying 257500, China. Electronic address:
Due to the endocrine toxicity, neurotoxic, and reproductive toxicity to organisms, the sources and risks of brominated organic pollutants have attracted widespread attention. However, knowledge gaps remain in the bromination processes of emerging phenolic pollutants in plants, which may increase the potential health risk associated with food exposure. Our study discovered that light induced generation and accumulation of more toxic brominated organic compounds (Br-org) in lettuce leaves under the stress of acetaminophen (ACE) than that without light, as evidenced by an increase in C-Br bond intensity in FTIR analysis.
View Article and Find Full Text PDFA Robust -Symmetric Aluminate Hydride for CO Hydroboration Catalysis: Mechanistic Insights and Countercation Influence on Catalytic Performance.
Inorg Chem
January 2025
Institute of Chemistry, Université de Strasbourg, CNRS, Strasbourg 67000, France.
The present study details the synthesis and characterization of a robust, monomeric Al-H aluminate supported by a tridentate -phenolate ligand, isolated as [][Li(THF)] and [][N(Bu)] salts, which were then exploited as CO hydroboration catalysts. As initial reactivity studies, it was observed that the nucleophilic Al-H anion in [][C] (C = countercation [Li(THF)] or [N(Bu)]) reacts fast with CO, to afford the corresponding Al-formate complexes [][C], which were isolated and structurally characterized. Such anions were then exploited as potential CO reduction catalysts.
View Article and Find Full Text PDFDichlorination of olefins with trichloroisocyanuric acid (TCCA) and tetrabutylammonium chloride (TBACl).
Org Biomol Chem
January 2025
Department of Chemistry, Faculty of Arts and Sciences, Amasya University, Amasya, Turkey.
Herein, a new metal-free, molecular chlorine-free, environmentally friendly, atom-economical, short time, inexpensive and simple operation method with mild reaction conditions for chlorination of alkenes, cyclic alkenes, ,-unsaturated carbonyl compounds, heteroaromatics, and natural products was reported with up to 96% yields using trichloroisocyanuric acid (TCCA) as the electrophilic chlorine source and TBACl as the nucleophilic chlorine source. It was demonstrated with bicyclic alkene benzonorbornadiene that regioselective chlorobromination and dibromination reactions can be carried out through TCCA/TBABr redox reactions, where TCCA acts as an oxidant in the presence of TBABr. The structures of the redox products were confirmed as a result of control experiments conducted with the newly presented DBI/TBACl and DBI/TBABr halogenation pairs.
View Article and Find Full Text PDFA deoxyfluoroalkylation-aromatization strategy to access fluoroalkyl arenes.
Chem Commun (Camb)
January 2025
Borch Department of Medicinal Chemistry, Purdue University, West Lafayette, IN, 47906, USA.
Fluoroalkyl arenes (Ar-R) are valuable substructures present in several FDA-approved drugs, patents, agrochemicals, and materials, and complementary strategies that enable access to a broad spectrum of Ar-R compounds benefit these applied fields. Herein, we report a deoxyfluoroalkylation-aromatization strategy to convert cyclohexanones into broad-spectrum Ar-R containing compounds. Generally, the fluoroalkyl sources were activated to participate in a 1,2-addition reaction followed by aromatization in a sequence that contrasts more common preparations of these Ar-R compounds, such as (i) transition-metal catalyzed cross-coupling reactions of aryl electrophiles and nucleophiles, and (ii) radical fluoroalkylation reactions of C-H bonds of arenes.
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!