73520-87-3Relevant academic research and scientific papers
Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage
Zhao, Jian-Nan,Kayumov, Muzaffar,Wang, Dong-Yu,Zhang, Ao
, p. 7303 - 7306 (2019/10/02)
Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.
C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
Xuan, Maojie,Lu, Chunlei,Lin, Bo-Lin
supporting information, (2019/08/26)
An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition-elimination mechanism.
The [Cu]-catalyzed SNAR reactions: Direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II) - Ascorbate redox system
Goriya, Yogesh,Ramana
experimental part, p. 7642 - 7650 (2010/12/19)
A one pot [Cu]-promoted SNAr reaction of electron-deficient halobenzenes with sodium azide and the reduction of the intermediate aryl azides under the same Cu(II)-ascorbate redox conditions leading to anilines has been documented. Control experiments revealed that both ascorbate and proline play important role in the reaction path way. Further, the use of this catalytic Cu(II)-ascorbate redox system has been explored for the synthesis of arylthioethers.
Palladium on charcoal as a recyclable catalyst for C - S cross-coupling of thiols with aryl halides under ligand-free conditions
Jiang, Zheng,She, Jin,Lin, Xufeng
supporting information; experimental part, p. 2558 - 2562 (2009/12/28)
5-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides using a catalytic amount of palladium on charcoal as a heterogeneous catalysis with potassium hydroxide as the base in dimethyl sulfoxide (DMSO) at 110°C is accomplished in good yields. The C. - S bond formation reaction functions under ligand-free conditions, and the palladium on charcoal catalyst can be is reused for five runs without any loss of activity.
Nucleophilic aromatic substitution reaction of nitroarenes with alkyl- or arylthio groups in dimethyl sulfoxide by means of cesium carbonate
Kondoh, Azusa,Yorimitsu, Hideki,Oshima, Koichiro
, p. 2357 - 2360 (2007/10/03)
Treatment of nitroarenes having electron-withdrawing groups at the ortho or para position with alkanethiol in the presence of cesium carbonate in dimethyl sulfoxide at 25°C leads to nucleophilic displacement of the nitro group with the alkylthio group. Cesium carbonate is superior to other bases such as potassium carbonate, sodium carbonate, and triethylamine. The cesium-mediated nucleophilic aromatic substitution reaction provides a mild yet powerful and user-friendly protocol for the synthesis of aryl sulfides.
Synthesis and in vitro antifungal activity of 4-substituted phenylguanidinium salts
Braunerova, Gabriela,Buchta, Vladimir,Silva, Luis,Kunes, Jiri,Palat Jr., Karel
, p. 443 - 450 (2007/10/03)
A series of 4-substituted phenylguanidinium derivatives was synthesized and its antimicrobial activity was evaluated in vitro against eight potentially pathogenic strains of fungi.
The use of aminoiminomethanesulfinic acid (thiourea dioxide) under phase transfer conditions for generating organochalcogenate anions. Synthesis of sulfides, selenides and tellurides
Comasseto, J. V.,Lang, E. S.,Ferreira, J. Tercio B.,Simonelli, F.,Correira, V. R.
, p. 329 - 340 (2007/10/02)
A procedure is described which allows for the in situ synthesis of arylalkyl, diaryl and dialkylchalcogenides under phase transfer conditions starting from the corresponding diorganodichalcogenides.The dichalcogenides are reduced by aminoiminomethanesulfinic acid (thiourea dioxide) in alkaline medium and catalyzed by a quaternary ammonium salt.The reduction proceeds easily for diaryl disulfides and diaryl diselenides at a sodium hydroxide concentration of 13percent; diaryl ditellurides require a 50percent sodium hydroxide solution to give the aryl tellurolate anion.The dialkyl diselenides and dialkyl ditellurides are more difficult to reduce.The intermediate arylthiolates and arylselenolates are quenched by alkyl and activated aryl halides to give the corresponding sulfides and selenides in high yield (77-97percent).The aryltellurolates react with alkyl halides giving the aryl alkyl tellurides in 81-96percent yield.The procedure could not be successfully used for the synthesis of dialkylselenides and dialkyl tellurides; low yields and mixture of products were formed.
