5097-95-0Relevant academic research and scientific papers
Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
, p. 2707 - 2712 (2020/03/11)
An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 3048 - 3055 (2019/03/21)
A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
Palladium-Catalyzed Enantioselective C?H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization
Zhu, Yu-Chao,Li, Yan,Zhang, Bo-Chao,Zhang, Feng-Xu,Yang, Yi-Nuo,Wang, Xi-Sheng
supporting information, p. 5129 - 5133 (2018/03/27)
The first example of PdII-catalyzed enantioselective C?H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) throu
Diarylation of chalcogen elements using arylboronic acids via copper- or palladium-catalyzed oxidative coupling
Taniguchi, Nobukazu
, p. 5818 - 5823 (2016/08/30)
Transition metal-catalyzed diarylations of sulfur, selenium and tellurium were achieved using arylboronic acids in air. A copper-catalyzed reaction of sulfur or selenium efficiently yielded numerous symmetrical diaryl sulfides or selenides in the presence of NH4BF4. However, the diarylation of tellurium was not possible using this method, and required a palladium catalyst in the presence of KI and air for the reaction to proceed.
Efficient synthesis of diaryl sulfides by copper-catalysed coupling of aryl halides and thioacetate in water
Zhang, Yimin,Liu, Li,Chen, Junmin
, p. 19 - 21 (2013/04/10)
A simple economical, and highly efficient catalytic system for the synthesis of diaryl sulfides by a copper-catalysed coupling of aryl halides and thioacetate in water has been developed. A variety of aryl halides reacted with thioacetate to give the desired products in high yields up to 95%. The present catalysis protocol tolerated a wide range of functional groups, including amino, fluoro, and carboxyl moieties.
Efficient copper-catalyzed double S-arylation of aryl halides with sodium sulfide in PEG-400
Chen, Junmin,Zhang, Yimin,Liu, Li,Yuan, Tangjun,Yi, Fei
, p. 1284 - 1290 (2012/11/07)
An efficient copper-catalyzed double S-arylation of sodium sulfide with aryl halides in PEG-400 has been developed. With CuI as a catalyst and PEG-400 as a solvent, a range of electron-withdrawing or electron-donating aryl iodides and aryl bromides were found to be applicable to the environmentally benign system. The present procedure is mild and tolerant of a variety of functional groups and the steric hindrance of ortho-substituents on aryl halides did not affect the outcome of good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Efficient copper(I)-catalyzed S-arylation of KSCN with aryl halides in PEG-400
Li, Xiaokang,Yuan, Tangjun,Chen, Junmin
experimental part, p. 651 - 655 (2012/05/05)
A simple and efficient protocol for CuI-catalyzed C-S bond formation of aryl halides with KSCN to symmetrical diaryl sulfides was reported in PEG-400 without any other additives. A variety of aryl halides were converted to the corresponding diaryl sulfides in good to excellent yields. The present procedure tolerated a variety of functional groups and the steric hindrance of ortho-substituents on aryl halides did not affect the outcome.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XLII. REACTION OF HALOGENOARENES AND 2-CHLOROTHIOPHENE WITH HYDROGEN SULFIDE IN THE PRESENCE OF ACETYLENE
Deryagina, E. N.,Korchevin, N. A.,Sukhomazova, E. N.,Russavskaya, N. V.,Voronkov, M. G.
, p. 1863 - 1867 (2007/10/02)
Benzothiophenes are formed with yields of more than 77percent in a single preparative stage during the gas-phase reaction of halogenoarenes with hydrogen sulfide and acetylene (600-700 deg C).It is suggested that arylthiyl radicals (ArS-radical), which are effectively captured by the acetylene, participate in the process.The effect of the structure of the halogenoarene on the selectivity of the process is discussed.The gas-phase reaction of 2-chlorothiophene with hydrogen sulfide in the presence of acetylene leads to the formation of thienothiophene.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVII. REACTIONS OF ALKANETHIONES WITH THE CHLORINE DERIVATIVES OF BENZENE, THIOPHENE, AND NAPHTHALENE
Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.
, p. 755 - 760 (2007/10/02)
Alkanethiols react effectively with chlorobenzene, its derivatives, 1-chloronaphthalene, and 2-chlorothiophene at 600-660 deg C with the preferential formation of the corresponding aromatic or heteroatomic thiols.Ethanethiol is most reactive.When it is used instead of hydrogen sulfide in reactions with chlorobenzene or its 4-substituted derivatives, the yield of the aromatic thiols, from which the phenylthiyl radicals are generated with greater difficulty, increases more sharply than the yield of the thiophenols, which generate the more stable 4-XC6H4S radicals.The side products of the reactions are the corresponding diaryl sulfides, thiophene, benzothiophene, and toluene.
