1216-95-1Relevant academic research and scientific papers
Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate
Gund, Sitaram Haribhau,Shelkar, Radheshyam Suresh,Nagarkar, Jayashree Milind
, p. 62926 - 62930 (2015)
Aryl sulfones have been for the first time synthesized by the reaction of sodium p-toluenesulfinate and arenediazonium salts using a CuI catalyzed homogeneous system. The developed protocol is a simple and efficient new route for the synthesis of diaryl sulfones with excellent product yields. The mild reaction conditions tolerate a range of functional groups. The best results were obtained with CuI, N,N′-dimethylethylenediamine, TBAI and K2CO3 in dimethyl sulfoxide at 100°C under an inert atmosphere.
Sodium periodate catalyzed selective sulfonylation of aromatics
Bandgar,Kamble
, p. 1066 - 1067 (2002)
Sodium periodate catalyzed sulfonylation of aromatics with p-toluenesulfonyl chloride gives the corresponding sulfones in good yield under neutral conditions.
Copper-Catalyzed Sulfonylation of Arylboronic Acids in Ionic Liquids
Kantam, M. Lakshmi,Neelima,Sreedhar,Chakravarti, Rajashree
, p. 1455 - 1458 (2008)
Cupric acetate in ionic liquids (ILs) catalyzes coupling reaction of arylboronic acids with sulfinic acid salts to afford aryl sulfones in good yields under ambient conditions. This mild and efficient cross-coupling reaction gives access to a wide range of alkylaryl and diaryl sulfones in good yields. The use of ionic liquid allows for easy separation of the product and recycling of copper catalyst.
Unsymmetrical Diaryl Sulfones through Palladium-Catalyzed Coupling of Aryl Iodides and Arenesulfinates
Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Parisi, Luca M.
, p. 4719 - 4721 (2002)
(Equation Presented) The palladium-catalyzed coupling of aryl iodides and arenesulfinates provides a simple and extremely efficient new route to unsymmetrical diaryl sulfones, usually isolated in high yield. The reaction tolerates a variety of functionalized aryl iodides, including those containing ether, ester, and nitro groups. The best results have been obtained by using Pd2(dba)3, Xantphos, Cs2CO3, and nBu4NCl in toluene at 80 °C.
Copper-assisted displacement reaction of nonactivated iodoarenes with arenesulfinates. Convenient alternative synthesis of unsymmetrical diaryl sulfones
Suzuki,Abe
, p. 6239 - 6242 (1995)
In the presence of copper(I) iodide in hot N,N-dimethylformamide (DMF), a variety of functionalized iodarenes undergo nucleophilic displacement reaction with sodium arenesulfinates to give the corresponding unsymmetrical diaryl sulfones in moderate to good yields.
Nano copper catalyzed synthesis of symmetrical/unsymmetrical sulfones from aryl/alkyl halides and p-toluenesulfonylmethylisocyanide: TosMIC as a tosyl source
Phanindrudu, Mandalaparthi,Jaya, Pogula,Likhar, Pravin R.,Tiwari, Dharmendra Kumar
, (2020)
A magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of diaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. Sulfones containing molecules have medicinal relevance as they are known to possess various activities such as antifungal, anti-HIV, antitumor, and anticancer. Herein, a magnetically induced nano copper-catalyzed efficient and mild route for the synthesis of biaryl and alkyl/aryl sulfones from aryl/alkyl halides and tosylmethyl isocyanide (TosMIC) has been developed. A variety of aryl and alkyl sulfones have been obtained in very good to excellent yields. In this newly developed protocol TosMIC acts as sulfonyl source. The catalyst can magnetically be recovered and recycled five times without significant loss in activity.
Synthesis of sulfones using sodium perchlorate as a catalyst under neutral conditions
Bandgar,Kamble,Fulse,Deshmukh
, p. 1105 - 1107 (2002)
Sulfonylation of aromatics with p-toluenesulfonyl chloride in the presence of a catalytic amount of sodium perchlorate gives the corresponding sulfones. Selectivity and neutral condition are the attractive features of this methodology.
Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates
Cheng, Lan,Guo, Jianbo,Li, Yufei,Liang, Xin,Wang, Qingmin,Xia, Qing,Zhang, Pei,Zhang, Weihua
supporting information, p. 8865 - 8870 (2021/11/30)
This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.
A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling
Adenot, Aurélien,Anthore-Dalion, Lucile,Nicolas, Emmanuel,Berthet, Jean-Claude,Thuéry, Pierre,Cantat, Thibault
supporting information, p. 18047 - 18053 (2021/11/16)
An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO2 molecule.
Sulfonylation of Bismuth Reagents with Sulfinates or SO2through BiIII/BiV Intermediates
Zhao, Fengqian,Wu, Xiao-Feng
supporting information, p. 2400 - 2404 (2021/07/28)
Studies to explore the catalytic activities of main-group elements are attractive. We report here our study of sulfonylation of bismuth reagents with sulfinates or SO2 surrogates. Under oxidative conditions, triarylbismuthines and sulfinates were transformed into diaryl sulfones. A transition-metal-like two-electron redox process at the Bi center was achieved in this reaction. Sulfur dioxide generated in situ can also replace sulfinates to deliver the corresponding symmetric diaryl sulfones. A rational mechanism for this reaction was also proposed that involves a Bi(III)-Bi(V) manifold.
