Background: The sulfonyl groups are general structural moieties present in agrochemicals, pharmaceuticals, and natural products. Recently, many efforts have been focused on developing efficient procedures for preparation of organic sulfones.
Materials And Methods: Water, a proton source, is considered one of the most ideal and promising solvents in organic synthesis for its easy availability, low cost, nontoxic and nonflammable characteristics. From the green and sustainable point of view, more and more reactions are designed proceeding in water.
Objective: The review focuses on recent advances of sulfonylation reactions proceeding in water. Sulfonylation reactions using sodium sulfinates, sulfonyl hydrazides, sulfinic acids, and sulfonyl chlorides as sulfonating agents were introduced in detail.
Results And Discussion: In this review, sulfonylation reactions proceeding in water developed in recent four yields were presented. Sulfonylation reactions using water as solvent have attracted more and more attention because water is one of the most ideal and promising solvents in organic synthesis for its facile availability, low cost, nontoxic and nonflammable properties.
Conclusion: Numerous sulfonating agents such as sodium sulfinates, sulfonyl hydrazides, sulfinic acid, sulfonyl chlorides and disulfides are efficient for sulfonylation reactions which proceed in water.
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http://dx.doi.org/10.2174/1570179417666200316124107 | DOI Listing |
Org Lett
January 2025
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, 79 West Yingze Street, Taiyuan 030024, People's Republic of China.
A solvent-controlled unprecedented tandem reaction of readily accessible SeO, a wide variety of sulfonyl hydrazides, and alkynes has been established for the chemodivergent construction of structurally complex 1,2-bis(()-1-aryl-2-arylsulfonylvinyl)diselanes and bis(()-1-aryl-2-(arylsulfonyl)vinyl)selanes via a catalyst-free one-pot three-component approach, respectively. The adjustable and controlled synthetic strategy shows good yields and chemoselectivities for most substrates under mild and simple conditions.
View Article and Find Full Text PDFChemistry
December 2024
Eotvos Lorand University, Organic Chemistry, Pazmany Peter Setany 1/A, 1117, Budapest, HUNGARY.
The present study reveals an unexpected anomaly observed in the acid-catalyzed hydrolysis of the 5,6-O-isopropylidene group in 3-O-protected D-gluco- and D-allofuranose derivatives. Although the removal of the 5,6-O-isopropylidene protecting group is typically rapid and quantitative under acidic conditions, an unexpected inhibition of this reaction is observed for the two C3-epimers, 3-O-imidazole sulfonyl moiety. X-ray data show a two-faced imidazole ring orientation in the crystal, while solution state NOE data reveal a critical interaction type between the isopropylidene and the imidazole rings.
View Article and Find Full Text PDFJ Org Chem
December 2024
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 PDFJ Org Chem
December 2024
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.
In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.
View Article and Find Full Text PDFOrg Lett
December 2024
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.
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