Copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol
The expedient and efficient copper powder catalyzed direct ring-opening arylation of benzazoles with aryl iodides in polyethylene glycol that proceeds in the absence of an added ligand has been developed. The protocol provides facile access to 2-(arylthio)anilines and 2-phenoxyanilines in high yields with a wide tolerance of functional groups. Transmission electron microscopy confirmed that the active catalyst results from the in situ generation of copper nanoparticles under standard reaction conditions, which is an alternative avenue to develop a highly effective metallic copper catalyst. Moreover, the catalytic system can be recycled up to six times. Copyright
Yao, Lifang,Zhou, Qing,Han, Wei,Wei, Shaohua
supporting information
p. 6856 - 6860
(2013/02/22)
Unexpectedly ligand-free copper-catalyzed C-S cross-coupling of benzothiazole with aryl iodides in aqueous solution
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.
One-pot synthesis of amine-substituted aryl sulfides and benzo[ b ]thiophene derivatives
A series of amine-substituted aryl sulfides have been synthesized from nitroaryl halides via a simple one-pot procedure involving metal-free C-S cross-coupling and in situ nitro group reduction. Various nitroaryl halides were reacted with thiols in recyclable poly(ethylene glycol) to afford the amine-substituted aryl sulfides in high yield. Additionally, the cross-coupling reactions of nitro- and aldehyde-substituted aryl halides with benzyl thiols under the same reaction conditions were demonstrated to afford benzothiazole and phenylbenzo[b]thiophene derivatives.
Duan, Zhongyu,Ranjit, Sadananda,Liu, Xiaogang
supporting information; experimental part
p. 2430 - 2433
(2010/07/10)
New potent inhibitors of trypanothione reductase from Trypanosoma cruzi in the 2-aminodiphenylsulfide series
From a screening assay, 2-aminodiphenylsulfides were selected as leads for trypanothione reductase (TR) inhibition and studied by molecular modelling in the catalytic site of the enzyme. A series of analogues, monomers or bis-derivatives, were synthesized to improve binding energy and therefore inhibiting potency. These compounds appeared to be mixed competitive TR inhibitors and their inhibition profile could be explained when their aggregation in solution was taken into consideration. A bis-aminodiphenylsulfide with an IC50 of 0.55 μM was revealed to be the best TR inhibitor described so far.