- Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
-
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
- Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
-
p. 2447 - 2458
(2020/04/15)
-
- Ascorbic Acid Promoted Metal-Free Synthesis of Aryl Sulfides with Anilines Nitrosated in Situ by tert -Butyl Nitrite
-
A mild, metal-free synthesis of aryl sulfides has been disclosed. Aryl diazonium ion was generated by the in situ nitrosation of aniline, and it was reduced by ascorbic acid (vitamin C) to form aryl radical, which underwent a thiolation with disulfide to yield aryl sulfide. The reaction proceeded smoothly without heating or irradiation. This strategy was also expanded to the synthesis of aryl selenides.
- Bu, Mei-Jie,Lu, Guo-Ping,Cai, Chun
-
supporting information
p. 1841 - 1846
(2015/08/06)
-
- 4,4′-diarylsulfanyl-2,2′,5,5′-tetraoxybiaryl derivatives as a water-soluble fluorescent dye
-
4,4′-Disulfanyl-2,2′,5,5′-tetrahydrobiaryl (5,5′-disulfanyl hydroquinone dimer) derivatives were readily synthesized from benzoquinone and thiols via an oxidative coupling reaction. The hydroquinone dimers showed strong fluorescence upon excitation at 330
- Kamimura, Akio,Nokubi, Tomomi,Watanabe, Ryusuke,Ishikawa, Mari,Nasu, Kotaro,Uno, Hidemitsu,Sumimoto, Michinori
-
p. 1068 - 1083
(2014/03/21)
-
- Transition-metal-free synthesis of unsymmetrical diaryl chalcogenides from arenes and diaryl dichalcogenides
-
A transition-metal-free synthetic method has been developed for the synthesis of unsymmetrical diaryl chalcogenides (S, Se, and Te) from diaryl dichalcogenides and arenes under oxidative conditions by using potassium persulfate at room temperature. Variously substituted arenes such as anisole, thioanisole, diphenyl ether, phenol, naphthol, di- and trimethoxy benzenes, xylene, mesitylene, N,N-dimethylaniline, bromine-substituted arenes, naphthalene, and diaryl dichalcogenides underwent carbon-chalcogen bond-forming reaction to give unsymmetrical diaryl chalcogenides in trifluoroacetic acid. To understand the mechanistic part of the reaction, a detailed in situ characterization of the intermediates has been carried out by 77Se NMR spectroscopy by using diphenyl diselenide as the substrate. 77Se NMR study suggests that electrophilic species ArE+ is generated by the reaction of diaryl dichalcogenide with persulfate in trifluoroacetic acid. The electrophilic attack of arylchalcogenium ion on the arene may be responsible for the formation of the aryl-chalcogen bond.
- Prasad, Ch Durga,Balkrishna, Shah Jaimin,Kumar, Amit,Bhakuni, Bhagat Singh,Shrimali, Kaustubh,Biswas, Soumava,Kumar, Sangit
-
p. 1434 - 1443
(2013/03/29)
-
- Silver catalyzed C-C and C-S coupling of aryl halides and thiols with boronic acids
-
An efficient Ag(I) catalyzed carbon-carbon and carbon-sulfur bond formation reaction of aryl halides and thiols with boronic acids has been demonstrated. Using this protocol, substrates with a wide range of functional group including electron-rich, and electron deficient substituents have been explored. These reactions are particularly useful to prepare symmetrical and unsymmetrical biphenyls and thioethers. These products were isolated in high yield.
- Das, Rima,Chakraborty, Debashis
-
p. 7023 - 7027
(2013/01/15)
-
- Bi(III)-catalyzed C-S cross-coupling reaction
-
A direct synthetic route for the C-S coupling of aryl halides with thiophenols is described. This method is tolerant to electron-withdrawing and electron-donating functional groups and also to the presence of functional groups in the ortho position of the aryl iodide or thiophenol. Aryl iodides are coupled with thiophenols without affecting the other functionalities present in the aryl ring. These reactions follow second-order kinetics. Copyright
- Malik, Payal,Chakraborty, Debashis
-
p. 557 - 561
(2013/01/15)
-
- Facile synthesis of quinone dimer derivatives substituted with sulfanyl groups and their properties
-
Quinone dimers are readily prepared quantitatively from 2- sulfanyl-1,4-dimethoxybenzene by oxidative treatment. The oxidative coupling progressed in a highly regioselective manner. Removal of O-protection and subsequent oxidation gave 5,5'- bis(sulfanylquinone) dimer in good yields. Physical properties of the dimer derivatives are also investigated.
- Kamimura, Akio,Nokubi, Tomomi,Nasu, Kotaro,Takechi, Yasuko,Ishihara, Yuriko,Kato, Kazunari,Noguchi, Saori,Watanabe, Masanori,Shirai, Masashi,Sumimoto, Michinori,Uno, Hidemitsu
-
p. 950 - 951
(2012/10/29)
-
- PHOTOCHEMICAL DESULPHURIZATION OF PHENOLIC THIOETHERS, THIOLS AND DISULPHIDES
-
Photolysis of alkylthiodihydroxybenzenes 2-4 and the related thiols 5, 6, 8 and disulphide 7 under argon proceeds with partial desulphurization to give the parent hydroxybenzenes in 13-36percent yield.Under the same conditions, benzenethiol, 9, decomposes slowly to give low amounts of benzene.Irradiation of sulphides 10 and 11 results in the selective cleavage of the C-S bond on the hydroxy- or methoxy-substituted ring to yield the desulphurized products in more than 60percent yield.
- d'Ischia, Marco,Testa, Gennaro,Mascagna, Donatella,Napolitano, Alessandra
-
p. 315 - 318
(2007/10/02)
-