13249-96-2

Upstream product

• 7570-98-1 1-naphthyl phenyl sulfide 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 91-20-3 naphthalene 
• 98-09-9 benzenesulfonyl chloride 
• 98-11-3 benzenesulfonic acid 
• 930-69-8 sodium thiophenolate 
• 13922-41-3 1-Naphthylboronic acid 
• 873-55-2 sodium benzenesulfonate 
• 90-14-2 1-Iodonaphthalene 
• 780-69-8 triethoxyphenylsilane 
• 66003-76-7 Diphenyliodonium triflate 
• 90-11-9 1-Bromonaphthalene 
• 122776-45-8 1-(phenylsulfinyl)naphthalene 
• 60-29-7 diethyl ether 

Relevant academic research and scientific papers

A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling

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.

Pd/NHC-catalyzed arylsulfonylation of boronic acids: A general and direct protocol to access diarylsulfones

For the first time, robust NHC-Pd complexes have been demonstrated as highly efficient catalysts in the direct arylsulfonylation of boronic acids. Remarkably, a broad number of diaryliodonium salts as powerful electrophilic arylation reagents are well compatible to form functional ortho-substituted diarylsulfones in satisfactory yields. Owing to the stronger σ-donor and weaker π-acceptor properties, the acenaphthoimidazolylidene ligands exhibit higher catalytic activities towards this challenging one-step arylsulfonylation reaction.

Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions

A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.

An efficient Cu-catalyzed microwave-assisted synthesis of diaryl sulfones

An efficient and microwave-assisted simple protocol for the synthesis of symmetrical/asymmetrical diaryl sulfones through the Cu(II)-catalyzed reaction of sodium salt of sulfinic acid with aryl boronic acid has been described. Various diaryl sulfones have been synthesized in very short reaction times with moderate to very good yields. Additionally, the method is also useful for the synthesis of aryl vinyl sulfones.

CuI catalyzed sulfonylation of organozinc reagents with sulfonyl halides

In this study, a facile CuI catalyzed synthesis of sulfones involving a nucleophilic addition of functionalized organozinc reagents to organic sulfonyl chlorides is realized. This reaction proceeds efficiently at room temperature, giving rise to various functional group substituted sulfones, generally in moderate to high yields. The method provides a novel, simple, and promising strategy for functionalized sulfone synthesis in the research field of sulfur chemistry. the Partner Organisations 2014.

Sulfonylation of aromatic compounds with sulfonic acids using silica gel-supported AlCl3 as a heterogeneous Lewis acid catalyst

Silica gel-supported aluminum chloride (SiO2-AlCl3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The catalyst can be prepared easily with cheap starting materials and is stable (as a bench-top catalyst) and reusable.

Polystyrene supported Al(OTf)3: A stable, efficient, selective, and reusable catalyst for sulfonylation of arenes with sulfonic acids

Cross-linked polystyrene supported aluminium triflate (Ps-Al(OTf) 3) was found to be an efficient and chemoselective heterogeneous Lewis acid catalyst for the direct conversion of arenes to sulfones using sulfonic acids as sulfonylating agents. The solid acid catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency.

Sur le comportement cathodique inattendu des di-aryl sulfoxydes en solvant de tres faible acidite

When conducted in aprotic solvents the cathodic reduction of aromatic sulphoxides (only able to lead to an electron transfer under such conditions) does not afford the quantitative formation of the corresponding sulphides.On the contrary, one observes the conversion into a mixture sulphide/sulphone in a molar ratio 1/1 followed in most of the cases by the cathodic cleavage of the sulphone.Reasons for such a are analysed.

Reactions of Haloarenes with Thiolate Anions in Tetraglyme: Cmpetition between Electron Transfer and SNAr Mechanisms

The reaction of the bromo-substituted naphthalene 1 with the alkanethiolate anions 2a-b and arenethiolate 2c in tetraglyme gave the corresponding 1-naphthyl thio-ethers 3a-c.Thio-ethers 3a-c were oxidized to the corresponding sulfones 4a-c with m-chloroperoxybenzoic acid.The reaction of the dichloro-substituted anthracene 5a with 2b gave the disubstitution product 6a.The reaction of 9-bromoanthracene 5c with the alkanethiolate 2b gave 6b, whereas the reaction of 5c with the arenethiolate 2c gave a mixture of aubstitution product 6c and anthracene 7.The observation of the formation of both 6c and 7 is explained by the competition between substitution (SNAr) and electron-transfer (ET) mechanisms.Consistent with this interpretation, the reaction of the monochloro-substituted 5b, which has a higher-energy ?* orbital, with 2c gave 6c without the formation of 7.Zn/KOH in tetraglyme was shown to reduce the aryl halides 5b-c and thio-ether 6c to 7.

REACTION OF DIPHENYL DISULPHIDE WITH 1,8-DEHYDRONAPHTHALENE

The reaction of diphenyl disulphide with 1,8-dehydronaphthalene gives benzothioxantene(5), 1-naphthyl-phenyl-sulphide(6) and naphthothiet(7).Formation of these compounds is explained via the intermediacy of the radical species (8).