Sulfones have been attractive targets for synthetic organic chemists owing to their immense applications in medicinal, material, and synthetic chemistry. In this context, an efficient transition-metal-free process has been demonstrated, wherein a broad range of alkyl/aryl/heteroaryl sodium sulfinates react with varyingly substituted aryne precursors (o-silyl aryl triflates) under mild reaction conditions to afford structurally diverse sulfones in good to excellent yields.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol5018646 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Aerobic Copper-Catalyzed Hydroxysulfonylation of Vinylarenes with Sodium Sulfinates.
J Org Chem
January 2025
College of Chemistry and Chemical Engineering, Green Catalysis & Synthesis Key Laboratory of Xinyang City, Xinyang Normal University, Xinyang 464000, China.
A novel and efficient method for the intermolecular hydroxysulfonylation of vinylarenes using sodium sulfinates has been achieved through aerobic copper catalysis. This transformation proceeded smoothly with green air as the terminal oxidant in the presence of Cu (I)/1,10-phenanthroline as an efficient catalytic system, leading to an array of β-hydroxysulfones in moderate to high yields. The significant advantages of this protocol are the mild reaction conditions, readily available starting materials, good functional-group compatibility, synthetic convenience, and practicability.
View Article and Find Full Text PDFRecent progress in C-S bond formation electron donor-acceptor photoactivation.
Org Biomol Chem
January 2025
Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, China.
Recent advancements in C-S bond formation electron donor-acceptor (EDA) complex photoactivation have been remarkable. EDA complexes, which are composed of electron donors and acceptors, facilitate C-S bond construction under mild conditions through single-electron transfer events upon visible light irradiation. This review highlights the utilization of various sulfur-containing substrates, including diacetoxybenzenesulfonyl (DABSO), sulfonic acids, sodium sulfinates, sulfonyl chlorides, and thiophenols, in EDA-promoted sulfonylation and thiolation reactions, covering the works published since 2017 to date.
View Article and Find Full Text PDFFacile synthesis of 2-sulfonylbenzothiazoles cascade SO-NCS addition and S-C(sp) coupling.
Chem Commun (Camb)
January 2025
State Key Laboratory of NBC Protection for Civilian, Beijing 102205, P. R. China.
A new synthetic route to 2-sulfonylbenzothiazoles (BtsR) employing cascade SO-NCS nucleophilic addition and CuI-catalysed S-C(sp) coupling was developed. Structurally diverse BtsR molecules were readily afforded in high yields from the rapid and benign reaction of 2-iodoarylisothiocyanates with sodium sulfinates in DMSO, generally without the need for further column isolation.
View Article and Find Full Text PDFSolvent Controlled Chemodivergent Sulfonyl Addition into Enynones: Synthesis of α-Furyl Sulfones and Stereodefined Vinyl Sulfones.
J Org Chem
January 2025
Department of Chemistry, National Institute of Technology, Tiruchirappalli 620015, Tamilnadu, India.
Sodium salt of aryl sulfinic acid reacts with enynone in a different manner, yielding α-furyl sulfone and stereodefined vinyl sulfone in toluene and EtOH respectively in the presence of ZnCl. The salient features of this protocol include chemoselectivity, broad substrate scope, high efficiency, high yield, and easy purification. The synthetic utilities of the products are demonstrated by cycloaddition and cis-trans photoisomerization reactions.
View Article and Find Full Text PDFElectrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from -Alkynyl--(formyl)anilides and Sulfinates.
Org Lett
January 2025
Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya strasse, 6, 117198 Moscow, Russia.
Electrolysis of -alkynyl--(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates.
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!