3169-87-7Relevant academic research and scientific papers
Transition-Metal-Free Synthesis of N-Arylphenothiazines through an N- And S-Arylation Sequence
Matsuzawa, Tsubasa,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 2347 - 2352 (2021/04/05)
An efficient synthetic method of N-arylphenothiazines from o-sulfanylanilines under transition-metal-free conditions is disclosed. An N- and S-arylation sequence of o-sulfanylanilines enabled us to synthesize a wide variety of N-arylphenothiazines. In par
Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization
Luo, Kai,Yang, Wen-Chao,Wei, Kai,Liu, Yue,Wang, Jun-Ke,Wu, Lei
supporting information, p. 7851 - 7856 (2019/10/11)
A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.
Heterogeneous copper-catalyzed synthesis of S-arylated 2-aminothiophenols via ring opening of benzothiazoles and C-S coupling using aryl halides
Ichikawa, Tomohiro,Matsuo, Tomohiro,Tachikawa, Takumu,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
, p. 793 - 805 (2019/04/26)
Chelate resins, which are polystyrene-divinylbenezene-based polymers bearing iminodiacetic acids or polyamines as ligands, supported copper catalysts (Cu/CR11 or Cu/CR20) in effectively catalyzing the ring cleaving S-arylation of benzothiazole with aryl i
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.
Metal-Free Iodine-Catalyzed Direct Arylthiation of Substituted Anilines with Thiols
Yang, Daoshan,Yan, Kelu,Wei, Wei,Zhao, Jing,Zhang, Mengqi,Sheng, Xuguang,Li, Guoqing,Lu, Shenglei,Wang, Hua
, p. 6083 - 6092 (2015/06/30)
Iodine-catalyzed direct arylthiation of substituted anilines for the synthesis of various diaryl sulfides has been developed under metal- and solvent-free conditions. The present method uses readily available thiols as the arylthiation reagents, and envir
Palladium Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer (Pd np -nSTDP) as Catalyst in the Synthesis of Mono-, Di-, and Trisulfides through C-S Cross-Coupling Reactions
Isfahani, Amir Landarani,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Moghadam, Majid,Khosropour, Ahmad Reza,Tangestaninejad, Shahram,Nasr-Esfahani, Mahboobeh,Rudbari, Hadi Amiri
supporting information, p. 645 - 652 (2014/04/03)
A wide variety of diaryl sulfides has been synthesized in excellent yields via C-S cross-couplings of aryl/heteroaryl halides with aromatic/heteroaromatic thiols in the presence of palladium nanoparticles immobilized on nanosilica triazine dendritic polymer (Pd np -nSTDP) as a reusable catalyst under thermal conditions and microwave irradiation. Pd np -nSTDP also showed excellent catalytic activity for the preparation of a series of di- and trisulfides with benzene, pyridine, pyrimidine, and/or 1,3,5-triazine as the central cores by one-pot multi C-S cross-coupling reactions. Georg Thieme Verlag Stuttgart. New York.
Efficient C-S cross-coupling of thiols with aryl iodides catalyzed by Cu(OAc)2·H2O and 2,2′-biimidazole
Zong, Chenglong,Liu, Jianli,Chen, Shengyan,Zeng, Runsheng,Zou, Jianping
supporting information, p. 212 - 218 (2014/04/03)
The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. The classical Ullmann C-S cross coupling reaction of aryl iodides with aromatic/alkyl thiols under catalysis of 15 mol% Cu(OAc)2· H2O and 15 mol% 2,2′-biimidazole works at 80°C in DMSO for 3 h to provide a variety of aryl sulfides in good to excellent yields. Copyright
Unexpectedly ligand-free copper-catalyzed C-S cross-coupling of benzothiazole with aryl iodides in aqueous solution
Feng, Yi-Si,Qi, Hong-Xia,Wang, Wei-Cheng,Liang, Yu-Feng,Xu, Hua-Jian
supporting information; experimental part, p. 2914 - 2917 (2012/07/27)
A novel synthetic protocol for 2-aminophenyl sulfide derivatives via the reactions of benzothiazole with aryl iodides was reported for the first time. The reactions were catalyzed by CuCl with tetrabutylammonium hydroxide as the base and water as the solvent without ligand at 50°C or room temperature. A variety of aryl iodides underwent the C-S cross-coupling reaction with benzothiazole to afford smoothly the corresponding products in excellent yield.
Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor
Prasad,Sekar, Govindasamy
supporting information; experimental part, p. 1008 - 1011 (2011/05/08)
An efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers using potassium ethyl xanthogenate as a thiol surrogate is developed. This new protocol avoids usage of intricate thiols and makes use of its easily available xanthate as a precursor, and thiol will be generated in situ to prepare the diaryl thioethers through a Cu-catalyzed double arylation. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles. (Figure Presented)
Discovery and SAR development of 2-(phenylamino) imidazolines as postacyclin receptor antagonists
Clark, Robin D.,Jahangir, Alam,Severance, Daniel,Salazar, Rick,Chang, Thomas,Chang, David,Jett, Mary Frances,Smith, Steven,Bley, Keith
, p. 1053 - 1056 (2007/10/03)
On the basis of screening hits (1a,b), a series of selective, high affinity prostacyclin receptor antagonists was developed. The optimized lead compound 25d [(4,5-dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxybenzyl)phenyl] amine] had analgesic activity in the rat.
