20912-17-8Relevant articles and documents
Coupling of thiols and aromatic halides promoted by diboron derived super electron donors
Franco, Mario,Vargas, Emily L.,Tortosa, Mariola,Cid
supporting information, p. 11653 - 11656 (2021/11/12)
We have proven that pyridine-boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a SRN1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.
Rate and Yield Enhancements in Nucleophilic Aromatic Substitution Reactions via Mechanochemistry
Andersen, Joel M.,Starbuck, Hunter F.
, p. 13983 - 13989 (2021/04/02)
A variety of nucleophilic aromatic substitution reactions were carried out mechanochemically to great advantage. On average, reactions rates were nine-times faster. The corresponding kinetic studies presented provide the clearest head-to-head kinetic comparisons between mechanochemical and conventional systems at identical temperatures. Attempts are provided at classifying the kinetics of one example. Removal of polar, protic solvents from these reactions presents environmental benefits to a reaction class whose kinetics are heavily dependent on such solvents.
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.
Primary sulfonamide as a coupling partner: Copper(I)-catalyzed regioselective cross-coupling of 2-nitro benzenesulfonamides with thiol through the cleavage of Ar–SO2NH2 bonds
Chen, Junmin,Zhang, Kuo,Zhao, Yongli,Pu, Shouzhi
, p. 1316 - 1323 (2018/04/05)
In this article, we have presented a novel and efficient method for the direct synthesis of unsymmetrical sulfides through the copper(I)-catalyzed cross-coupling of 2-nitro benzenesulfonamides with thiols in the presence of catalytic amount of CuI in DMF as solvent at 100 °C. In addition, the products were obtained in high to excellent yields. More importantly, the novel system showed the primary 2-nitro benzenesulfonamides as a new coupling partner and regioselectively promoted C–S bond-forming transformations through the cleavage of Ar–SO2NH2 bonds.
NOVEL TRIAZINE COMPOUND, AND ORGANIC ELECTRONIC ELEMENT AND PLANT-GROWING LIGHTING THAT USE THE SAME
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Paragraph 0082, (2018/07/28)
PROBLEM TO BE SOLVED: To provide a triazine compound which has a high triplet energy level and excellent heat resistance, and can be used as an organic electronic element material realizing an element with high efficiency, low voltage and a long life. SOLUTION: In the triazine compound, as represented by the general formula [1] in the figure, a triazine backbone moiety is linked to a dibenzofuran or dibenzothiophene backbone moiety via a biphenyl backbone moiety, where X is an oxygen atom or sulfur atom. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
, p. 5580 - 5585 (2016/10/21)
A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
Aerobic copper-catalyzed decarboxylative thiolation
Li, Minghao,Hoover, Jessica M.
supporting information, p. 8733 - 8736 (2016/07/15)
Copper-catalyzed decarboxylative thiolation using molecular oxygen as the sole oxidant was developed. A variety of aromatic carboxylic acids including 2-nitrobenzoic acids, pentafluorobenzoic acid and several heteroaromatic carboxylic acids undergo efficient thiolation to furnish the aryl sulfides in moderate to excellent yields.
Iridium and phosphine promoted C-F bond activation: The C-S cross-coupling of aryl fluorides with diaryl disulfides to synthesize thioethers
Li, Liang,Miao, Hongyan,Ding, Yuqiang
supporting information, p. 6405 - 6408 (2015/11/16)
Carbon-fluorine bond is the strongest known single bond to carbon and proved very difficult to cleave. An iridium and phosphine promoted C-F bond activation was developed, for the first time achieving the C-S cross-coupling reaction of disulfides with aryl fluorides using iridium complex. The corresponding monoarylthiolation products were obtained at moderate to good yields. Thus, it represents a new method for the synthesis of aryl sulfides through C-F bond activation.
KF/clinoptilolite: An efficient promoter for the synthesis of thioethers
Salmanpour, Sadegh,Khalilzadeh, Mohammad A.,Hosseini, Abolfazl
, p. 339 - 344 (2013/07/28)
Potassium fluoride impregnated on natural zeolite as a new solid base system effectively catalyzes the coupling of thiophenols with electron-deficient fluoro-, chloro- and bromo-arenes in DMSO. This versatile and efficient solid base has been demonstrated to afford the corresponding desired products in good to excellent yields. This procedure provides a convenient, efficient and practical method for the preparation of diaryl thioethers.
Ligand-free solid supported palladium(0) nano/microparticles promoted C-O, C-S, and C-N cross coupling reaction
Bandna,Guha, Nitul Ranjan,Shil, Arun K.,Sharma, Dharminder,Das, Pralay
supporting information, p. 5318 - 5322 (2012/10/30)
Ligand-free solid-supported nano and microparticles of Pd(0) (SS-Pd) were used as a heterogeneous catalyst in carbon-heteroatom bond formation reactions. Nitro substituted aryl halides reacted with oxygen, sulfur, and nitrogen nucleophiles to afford the corresponding products in good yields. A one-pot sequential cross coupling and nitro-reduction was also performed using the same SS-Pd catalyst to access amine substituted carbon-heteroatomic molecules. In addition, SS-Pd could be recycled up to seven runs without a significant loss of catalytic activity.
