Latest ArticlesIn recent years, the transition metal-free sulfenylation of C-H bond for C-S formation has been rapidly advanced and has become an eco-friendly synthetic tool for pharmacists and organic chemists. Various natural or bioactive molecules such as (hetero)arenes, olefins, carbonyl compounds, alkanes, have been employed for sulfenylating reactions. This review will focus on the recent five-year advances in C-S bond formation via direct sulfenylation of C(sp3)-H bonds under metal-free conditions and elaborate their mechanisms from a new perspective.
An Ir-catalyzed selective mono-sulfamidation of 2-arylquinazolinones has been achieved with a low catalyst loading under mild conditions. A series of regioselective mono-sulfamided 2-arylquinazolinones were obtained in up to 90% yields. Compared with our previous work of constructing di-sulfamidated 2-arylquinazolinones, the mono-sulfamided products could be obtained selectively by changing the ratio of substrates, the loading of catalyst, acid additive, and reaction time.
The enantioselective total synthesis of the putative structure of versiquinazoline H and three diastereomers has been achieved, which allowed the revision of the stereochemistry of this natural product. This six-step total synthesis relied on the evolution of the strategy that we previously developed, which features a DMDO-triggered tandem reaction. The modification of the lactamization step resulted in a significant improvement of yield that ensured the efficient total synthesis.
Two novel 2-(4-(9, 9-disubstitued-9H-fluoren-2-yl)phenyl)-9, 9-diethyl-1-phenyl-1, 9-dihydrofluoreno-[2, 3-d]imidazole derivatives 2a and 2b were synthesized and characterized. Their photophysical and electrochemical properties, thermal stability property, and electroluminescence (EL) performance of 2b were investigated. The fabricated device based on 2b doping into 4, 4'-N, N'-dicarbazole-biphenyl (5%) as an emitter present a maximum brightness of 1272 cd/m2 at 4 V with the CIE coordinate of (0.1590, 0.0465).
A new and convenient visible-light-induced method has been developed for the synthesis of sulfonylated benzofurans via oxidative cyclization reaction of 1, 6-enynes and arylsulfinic acids. This reaction was carried out under metal-free and mild conditions, in which the C-S, C-C and C=O bonds could be sequentially formed in one pot operation.
Graphene-like C3N4/Ag3PO4 photocatalysts are synthesized by calcination and solutions precipitating method. The obtained g-C3N4/Ag3PO4 composites display excellent photocatalytic activity for the degradation of methylene orange (MO), rhodamine B (RhB) and tetracycline (TC) under visible light irradiation. The solutions containing RhB (10 mg/L) and MO (10 mg/L) can be efficiently degraded within 15 min and 30 min. Especially, nearly 80% of TC (50 mg/L) is degraded within 20 min, which are much better than those of pure g-C3N4 nanosheets and Ag3PO4, implying that strong interaction and reasonable energy band alignment in the contact interface can effectively transfer the carries. Furthermore, the g-C3N4/Ag3PO4 composites exhibit the improved stability, and only a slight decrease is observed after three recycling runs. Moreover, the impact of inorganic ions and PH values on the degradation performance is rather small. The Z-scheme photocatalytic mechanism of the g-C3N4/Ag3PO4 composites based on the active species trapping experimental is proposed. This work demonstrates the promising applications of the g-C3N4/Ag3PO4 composites in environmental issues.
A new artificial transmembrane channel molecule bearing dihydrogen phosphate groups has been synthesized. The terminal dihydrogen phosphate groups enable the channel to be highly negatively charged at both ends of the channel structures. The artificial channel could incorporate into the lipid bilayer efficiently under low concentration. The channel displays high NH4+/K+ selectivity due to the electrostatic interaction and hydrogen bonding between NH4+ and the terminal dihydrogen phosphate groups.
The condensation reaction of ω-aminoalkyleneamide-functionalized pillar[5]arenes with 2-(4-([2, 2':6', 2''-terpyridin]-4'-yl)phenoxy)acetic acid or 4-(4-([2, 2':6', 2''-terpyridin]-4'-yl)phenoxy)butanoic acid in dry chloroform at room temperature under the catalysis of HOBT/EDCl resulted in novel pillar[5]arene diamido-bridged terpyridine derivatives. 1H NMR and 2D NOESY spectra clearly indicated that the interesting [1]rotaxanes were formed by longer alkylene such as propylene, butylene and hexylenediamido chains threading into the cavity of the pillar[5]arene and with larger terpyridine acting as the stopper. However, the shorter ethylenediamido chain only exists outer of cavity of pillar[5]arene and the molecule exist on free form.
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 additionelimination mechanism.
Herein, we report a Pd-catalyzed mono-α-arylation reaction for pyridine benzylic functionalization. This approach serves as an efficient alternative to synthesize di-heteroaryl acetates in good yields and selectivities. Moreover, the method is applicable to heteroaryl substrate combinations, and exhibits great functional group tolerance. A streamlined protocol also enables the rapid synthesis of diheteroaryl ketones. The synthetic value was also demonstrated by scale-up experiments
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