A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones

Kumar, Dalip; Arun, V.; Pilania, Meenakshi; Shekar, K. P. Chandra

doi:10.1055/s-0032-1317803

Cited by 31 publications

(14 citation statements)

References 16 publications

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“…Both electron-rich and electrondeficient arylsulfinates react with bromobenzene efficiently (entries 10-14). The sterically hindered sodium arylsulfinates react slowly with bromobenzene to give the corresponding products (entries [15][16][17]. As shown in entries 9 and 18, we were able to extend the methodology to 2-naphthyl-containing compounds substrates in good yields.…”

Section: Resultsmentioning

confidence: 81%

“…Sequentially, the appropriate solvent for this reaction was investigated carefully in order to uncover optimum conditions (entries 10-18 using toluene, tetrahydrofuran, dimethoxyethane, acetonitrile, dimethylformamide, dimethylacetamide, dimethylsulfoxide, N-methyl-2-pyrolidone and DMI). Importantly, the reaction in aprotic polar solvents leads to higher yields as compared to other solvents (entries [13][14][15][16][17][18] and DMI is the highest yielding solvent.…”

Section: Resultsmentioning

confidence: 99%

“…[3][4][5] Recently, transition-metalcatalysed cross-coupling reactions have emerged as powerful tools for the construction of building blocks in a large number of compounds used as pharmaceuticals. 6,7 Sodium arylsulfinate has been used as an important aryl sulfonyl reagent to afford diaryl sulfones via cross-coupling with aromatic iodides, 8,9 aryl triflates, 10,11 diaryliodonium salts [12][13][14][15] and aryl boronic acids [16][17][18][19][20][21][22] (Fig. 1).…”

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confidence: 99%

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Cu(I)-Catalysed coupling of Arylsulfinic Salts with Aryl Bromides

Yao

2014

Journal of Chemical Research

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Section: Resultsmentioning

confidence: 81%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Cu(I)-Catalysed coupling of Arylsulfinic Salts with Aryl Bromides

Yao

2014

Journal of Chemical Research

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“…Diaryl sulfones 22 were synthesized by Kumar et al 26 via the metal-free, microwave-assisted arylation of sulfinate salts 21 in the presence of diaryliodonium salts. The reactions were conducted in PEG-400 at 50 °C.…”

Section: Scheme 9 Preparation Of Aryl Esters By O-arylationmentioning

confidence: 99%

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

Aradi

Tóth

Tolnai

et al. 2016

Synlett

193

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This account aims to give a description of the usefulness of diaryliodonium salts in organic chemistry, including their synthesis and applications in the presence and absence of transition metal catalysts. Herein, we briefly summarize the structural properties and reactivity of diaryliodonium salts. We collected several applications of the hypervalent reagents including metal-free arylations of C, O, N and S nucleophiles. Synthesis and functionalization of aromatic and heteroaromatic systems via copper and palladium catalyzed transformations are also discussed in this account.

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“…22 By employing diaryliodonium salts, we have recently developed high-yielding syntheses of diaryl sulfones and arylated azaheterocycles. 23,24 Herein, we wish to report a novel and metal-free direct O-arylation of quinolones utilizing readily available and stable diaryliodonium salts to access aryloxyquinolines (Scheme 1).…”

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confidence: 99%

Microwave-Assisted Metal- and Ligand-Free O-Arylation of Quinolones Using Diaryliodonium Salts: An Easy and Rapid Synthesis of Aryloxyquinolines

Mehra¹,

Tantak²,

Kumar³

et al. 2015

Synlett

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Table of contents 1 General Methods and Experimental Procedures S2 2 Analytical Data S4 3 Copies of 1 H and 13 C NMR Spectra S11 4 References S49 S2 1. General Methods and Experimental Procedures All of the reagents and solvents are commercially available and were used as purchased without any further purification. Some solvents except laboratory reagent grade were dried and purified, when necessary. Reactions were monitored by thin-layer chromatography (TLC) on pre-coated silica gel plates procured from Merck (silica gel 60, F 254, 0.25mm). Products were purified by column chromatography using 100-200 mesh silica gel and eluting with a hexane/ethyl acetate mixture. Melting points of the synthesized compounds were determined in E-Z melting point apparatus and are uncorrected. Mass spectra were recorded using Waters mass spectrometer. NMR (1 H & 13 C) spectra were recorded in Chloroform-d (CDCl 3) using Bruker-Avance II (400, 100 MHz) spectrometer and chemical shift are given in δ ppm units with respect to TMS as an internal standard. The proton multiplicities were mentioned as: s = singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublet and m = multiplet. Infrared spectra were recorded on Shimadzu IR Prestige-21 FT-IR spectrophotometer. Required diaryliodonium salts were synthesized using reported protocol. 1-3 S3 General procedure for the synthesis of 4-methyl-2-aryloxyquinoline (6). A mixture of 4 quinolone (0.62 mmol), diaryliodonium salt (0.62 mmol) and potassium carbonate (260 mg, 1.88 mmol) in toluene (1 mL) was irradiated in a CEM Discover MW reactor (100 W power) at 100 °C for 5 min. Upon completion of the reaction as indicated by TLC, solvent was removed and the residue was taken into dichloromethane (20 mL). To this solution, 20 mL of water was added and allowed to stir at room temperature for 10 min. The organic phase was separated, washed with brine solution (2 × 15 mL), dried over anhydrous Na 2 SO 4 and concentrated in vaccuo. The crude product thus obtained was purified through a silica gel (100-200) column chromatography to afford pure 4-methyl-2-aryloxyquinolines 6 in 62-81% yields. 4-Methyl-2-phenoxyquinoline (6a): Off white solid (119 mg, 81%); mp.: 76-77 °C (lit. 4 mp.:

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A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones

Cited by 31 publications

References 16 publications

Cu(I)-Catalysed coupling of Arylsulfinic Salts with Aryl Bromides

Cu(I)-Catalysed coupling of Arylsulfinic Salts with Aryl Bromides

Diaryliodonium Salts in Organic Syntheses: A Useful Compound Class for Novel Arylation Strategies

Microwave-Assisted Metal- and Ligand-Free O-Arylation of Quinolones Using Diaryliodonium Salts: An Easy and Rapid Synthesis of Aryloxyquinolines

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