3379-36-0Relevant articles and documents
Insertion of Benzyne and Substituted Benzynes into the S-S Bond of Diphenyl and Di-p-tolyl Disulfides Yielding the Corresponding o-Bis(arylthio)benzenes
Nakayama, Juzo,Tajiri, Takayuki,Hoshino, Masamatsu
, p. 2907 - 2908 (1986)
Benzyne and substituted benzynes undergo insertion into the S-S bond of diphenyl and di-p-tolyl disulfides to afford the corresponding o-bis(arylthio)benzenes in low but reproducible yields.
1,2-Bis(arylthio)arene synthesis: Via aryne intermediates
Mesgar, Milad,Nguyen-Le, Justin,Daugulis, Olafs
, p. 9467 - 9470 (2019)
Lithium 1,1-diadamantylamide (LDAM) base-promoted insertion of arynes into disulfide S-S bonds is described. After generation of arynes from readily available aryl halides and triflates, reactions with diaryl and diisopropyl disulfides afford the insertion products in moderate to excellent yields. Use of 1-cyclohexenyl triflate gave an excellent yield of 1,2-bis(phenylthio)cyclohexene.
Transformations of diphenyl sulfide and diphenylamine on aluminum chloride
Nekhoroshev,Gubaidullin,Yarkova,Nekhorosheva,Nifant’ev,Voronkov,Poleshchuk, O. Kh.,Tarasova
, p. 272 - 277 (2017)
Thianthrene has been synthesized by reacting diphenyl sulfide with AlCl3 in heptane at 98°C for 8 h at a diphenyl sulfide: AlCl3 molar ratio of 2: 1; the thianthrene yield is 58%. The reaction mechanism proposed previously has been confirmed by quantum-chemical calculations; the reaction is characterized by a low negative value of Gibbs free energy, a low heat of reaction, and a high activation energy of the first step. Diphenyl ether and diphenylamine do not enter the test reaction because of low nucleophilicity of the heteroatoms; diphenylamine dimerizes under the reaction conditions to form N,N′-diphenylbenzidine.
Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent
Shen, Guodong,Lu, Qichao,Wang, Zeyou,Sun, Weiwei,Zhang, Yalin,Huang, Xianqiang,Sun, Manman,Wang, Zhiming
supporting information, p. 184 - 198 (2021/09/20)
Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.
Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation
Yu, Fazhi,Mao, Runyu,Yu, Mingcheng,Gu, Xianfeng,Wang, Yonghui
, p. 9946 - 9956 (2019/09/04)
A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.
Disulfides as efficient thiolating reagents enabling selective bis-sulfenylation of aryl dihalides under mild copper-catalyzed conditions
Liu, Yunyun,Wang, Hang,Zhang, Jida,Wan, Jie-Ping,Wen, Chengping
, p. 19472 - 19475 (2014/05/20)
Selective bis-sulfenylation reactions of aryl dihalides have been achieved by copper-catalyzed C-S coupling reactions under mild conditions of refluxing EtOH (80 °C). Employment of disulfides as thiolating reagents enables the production of various bis(phenylthio)benzenes with excellent selectivity, and no products from mono C-S coupling are isolated. the Partner Organisations 2014.
Copper-catalyzed selective single arylsulfanylation of aryl diiodides with aryl thiols
Liu, Yunyun,Wang, Hang,Cao, Xiaoji,Fang, Zheng,Wan, Jie-Ping
, p. 2977 - 2982 (2013/11/06)
Selective single arylsulfanylation reactions of aryl diiodides with aryl or hetaryl thiols to give a broad array of iodine-functionalized sulfides were developed. Further elaboration of the iodine-containing products to provide a variety of aryl and hetaryl sulfides through coupling reactions was also demonstrated. Georg Thieme Verlag Stuttgart, New York.
Microwave-assisted Ullmann-Buchwald C-S bond formation using a copper(I) catalyst and trans-cyclohexane-1,2-diol as ligand
Bagley, Mark C.,Fusillo, Vincenzo,Hills, Edward G.B.,Mulholland, Alex T.,Newcombe, Joseph,Pentecost, Leanne J.,Radley, Emily L.,Stephens, Bethan R.,Turrell, Christopher C.
, p. 294 - 313 (2013/01/16)
Microwave irradiation of a thiophenol or alkyl thiol (1 equiv.) and an aryl halide (1 equiv.) in 2-propanol at 120°C for three hours in the presence of K2CO3 (2 equiv.) as base using copper(I) iodide as catalyst (5 mol%) and trans-cyclohexane-1,2-diol (2 equiv.) as ligand provides a rapid and convenient method for C-S bond formation. The process is most efficient using thiophenol and aryl iodide precursors, both of which may contain electron-donating and electronwithdrawing groups, to give the corresponding diaryl sulfide in good to excellent yield. ARKAT-USA, Inc.
Ligand-free highly effective iron/copper co-catalyzed formation of dimeric aryl ethers or sulfides
Qu, Xiaoming,Li, Tingyi,Zhu, Yan,Sun, Peng,Yang, Hailong,Mao, Jincheng
supporting information; experimental part, p. 5043 - 5046 (2011/08/22)
Highly selective coupling of diiodoarenes with phenols or phenthiols can be performed by using a low-cost, benign character and readily available Fe/Cu catalytic system in the absence of ligands. It is noteworthy that the desired dimeric aryl ethers or sulfides could be obtained in high yields by coupling between diiodoarenes and phenols, or diphenols with aryl iodides. The Royal Society of Chemistry 2011.
Efficient copper-catalyzed S-arylation of thiols with aryl bromides and chlorides
Li, Yaming,Li, Xiaoying,Wang, Huifeng,Chen, Tao,Xie, Yusheng
supporting information; experimental part, p. 3602 - 3608 (2010/12/19)
An efficient copper-catalyzed system for C-S cross-coupling of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity. Georg Thieme Verlag Stuttgart - New York.
