55709-45-0Relevant academic research and scientific papers
Palladium nanoparticles immobilized on a nano-silica triazine dendritic polymer: a recyclable and sustainable nanoreactor for C-S cross-coupling
Amiri Rudbari, Hadi,Landarani-Isfahani, Amir,Mirkhani, Valiollah,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram
, p. 21198 - 21205 (2020/06/26)
Dendrimers are of great interest due to their special structural topology and chemical versatility. Owing to their properties, dendrimers have found practical applications in catalytic processes as efficient nanoreactors. Therefore, we herein report an environmentally attractive strategy and highly efficient route for the synthesis of a wide variety of diaryl sulfides using palladium nanoparticles immobilized on a nano-silica triazine dendritic polymer (Pdnp-nSTDP) as a nanoreactor. In this manner, different diaryl or aryl heteroaryl sulfides and bis(aryl/heteroarylthio)benzene/anthracene/pyridine derivatives were preparedviaC-S cross-coupling reactions of aryl halides with diaryl/diheteroaryl disulfides under thermal conditions and microwave irradiation. The catalyst could be easily recovered and reused several times without any significant loss of its activity.
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.
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 ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
Feng, Yi-Si,Li, Yuan-Yuan,Tang, Lin,Wu, Wei,Xu, Hua-Jian
experimental part, p. 2489 - 2492 (2010/06/14)
We report a mild, convenient, environmentally friendly, and ligand-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI with KF/Al2O3 as the base, in DMF at 110 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and thiols.
p-Phenylene sulfide oligomers and their properties. Ar-S couplings mediated by copper or by fluorine substitutions
Goyot, Olivier,Gingras, Marc
scheme or table, p. 1977 - 1981 (2009/07/05)
A series of monodisperse p-phenylene sulfide oligomers were efficiently synthesized by using a bidirectional growth. A strategy combining Cu-catalyzed Ar-S couplings for small oligomers and fluorine aromatic substitutions by aryl thiolates for longer ones was put forward. The latter method is superior to Cu-catalyzed reactions for longer oligomers. Fluorine chemistry brings some new advantages such as solubility and reactivity. Qualitative crystallinity studies were reported according to the oligomer size and the functional series, by using a microscope equipped with a heating stage and a camera.
CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands
Deng, Wei,Zou, Yan,Wang, Ye-Feng,Liu, Lei,Guo, Qing-Xiang
, p. 1254 - 1258 (2007/10/03)
Novel mild conditions for the CuI-catalyzed coupling reactions of aryl iodides and bromides with aliphatic and aromatic thiols using amino acids as the ligand are reported.
Ring-opening reactions of 5-(aryl)thianthrenium bromides with aryl thiolates
Qian, Ding-Quan,Liu, Bo,Shine, Henry J.,Guzman-Jimenez, Ilse Y.,Whitmire, Kenton H.
, p. 139 - 147 (2007/10/03)
A series of 5-(aryl)thianthrenium bromides (6a-e) with aryl (Ar) groups phenyl (a), p-tolyl (b), p-anisyl (c), p-chlorophenyl (d) and p-bromophenyl (e) was prepared by reaction of thianthrene 5-oxide with the appropriate Grignard reagent ArMgBr. Reactions of 6a-e with aryl thiolates (Ar′SNa, Ar′ = phenyl, p-tolyl and p-chlorophenyl, 7a-c) were carried out in MeCN at room temperature. Products from 6a-c were a small amount of arene [benzene (8a) and toluene (8b)], and substantial amounts of ArSAr′ (9), thianthrene (Th) and a trisulfide, namely a 2-(ArS)-2′-(Ar′S)-diphenyl sulfide (10). Products from reactions of 6d,e were smaller amounts of 9 and 10 but substantial amounts of 1,4-di(Ar′S)benzene (11) and a tetrasulfide (12a-c). The reactions that lead to products 9-12 are attributed to ligand coupling (LC) pathways in sulfuranes formed by attack of Ar′S- at the sulfonium S atom of 6. In the formation of 11 and 12 the halogen atom (CI, Br) is first displaced from 6d,e by Ar′S-, giving a new thianthrenium ion (14) from which sulfurane formation (15) follows. Products 10 and 12 result from opening of the thianthrenium ring of sulfuranes 13 and 15 through LC. Products were assayed with a combination of GC and isolation with TLC, and were identified with a combination of GC (authentic compounds), x-ray crystallography (10a), elemental analyses and high-resolution mass spectrometry. The reactions of 6 are compared with earlier reactions of 5-(alkoxy)-and 5-(alkyl)thianthrenium salts (1 and 2). Copyright
