Yuqin Jiang

Cu(OAc)2·H2O/NH2NH2·H2O: an efficient catalyst system that in situ generates Cu2O nanoparticles and HOAc for Huisgen click reactions

A combination of Cu(OAc)2·H2O and NH2NH2·H2O, which in situ generates Cu2O-NPs and HOAc in water at room temperature, has been developed as a highly efficient catalytic system for Huisgen click reactions. Our results indicate that the in situ generated Cu2O-NPs and HOAc play important roles in the Huisgen click reaction.

Metallic copper wire: a simple, clear and reusable catalyst for the CuAAC reaction in supercritical carbon dioxide

An efficient protocol for the CuAAC reaction catalyzed by metallic copper wire for the synthesis of 1,4-disubstituted triazoles has been developed in supercritical carbon dioxide (scCO2) at 50 °C. The protocol could afford the corresponding products in excellent yields with a very easy work-up procedure. The metallic copper wire could be reused for more than 200 runs without decreasing the catalytic efficiency.

Carboxymethylpullulan promoted Cu2O-catalyzed Huisgen-click reaction

A combination of carboxymethylpullulan (CMP) and Cu2O has been developed as a highly efficient catalytic system for the Huisgen-click reaction. Our results indicate that the acidic CMP could be used for 6 cycles without decreasing the activating efficiency for Cu2O.

Preparation and characterization of stereocomplex aggregates based on PLA–P188–PLA

Novel dumbbell-shaped amphiphilic copolymers ((PLLA)2–G1–P188–G1–(PLLA)2 and (PDLA)2–G1–P188–G1–(PDLA)2) and linear-shaped amphiphilic copolymers (PLLA–P188–PLLA and PDLA–P188–PDLA) were synthesized by click chemistry and ring opening polymerization (ROP). The stereocomplexes (scPLA)2–G1–P188–G1–(scPLA)2 and scPLA–P188–scPLA were prepared and confirmed by X-ray diffraction (XRD). The stereocomplex interaction between PLLA and PDLA was firstly analyzed using microscale thermophoresis (MST) technology and the dissociation constant (Kd) was obtained as 342 μM. The aggregation behaviors of these stereocomplexes were studied using fluorescence spectroscopy, transmission electron microscopy (TEM) and light scattering (LS). The critical aggregate concentration (CAC) obtained from fluorescence measurements was 0.021 mg mL−1 for (scPLA)2–G1–P188–G1–(scPLA)2 and 0.042 mg mL−1 for scPLA–P188–scPLA. These stereocomplexes can self-associate in aqueous solution into spherical aggregates with a diameter of 181 nm for (scPLA)2–G1–P188–G1–(scPLA)2 and 222 nm for scPLA–P188–scPLA. Furthermore, the biocompatibility of the stereocomplexes was evaluated with a relatively lower cytotoxicity. Finally, DOX was encapsulated into the stereocomplex aggregates to evaluate the drug release ability in phosphate buffer at a pH value of 7.4 or 5.4. The drug loading content and the encapsulation efficiency of the aggregates are 9.8%, 54% for (scPLA)2–G1–P188–G1–(scPLA)2 and 8.2%, 45% for scPLA–P188–scPLA. The release of DOX at pH 5.4 is faster than that at pH 7.4. The pH value has a greater effect on the release rate of DOX from dumbbell-shaped stereocomplex aggregates than that from the linear-shaped ones, which ensures the long blood circulation and the higher DOX-release surrounding the tumor site.

An efficient CuI/DBU-catalyzed one-pot protocol for synthesis of 1,4-disubstituted 1,2,3-triazoles

A convenient CuI/DBU catalyzed one-pot method has been developed for the synthesis of 1,4-disubstituted 1,2,3-triazoles through the coupling of aryl iodides with sodium azide, followed by the intermolecular cyclization between the generated aryl azides and phenylacetaldehyde derivatives or alkynes in DMSO. The established protocol was compatible with a wide scope of substrates in good to excellent yields.

An efficient NaHSO 3 -promoted protocol for chemoselective synthesis of 2-substituted benzimidazoles in water

An efficient protocol for chemoselective synthesis of 2-substituted benzimidazoles from a variety of aliphatic/aromatic/heteroaryl aldehydes and o-phenylenediamine derivatives promoted by NaHSO3 in water had been developed. The amount of NaHSO3 had a great effect on the reaction selectivity of 2-substituted benzimidazole and 1,2-disubstituted benzimidazole when the reaction was carried out in water. When the amount of the NaHSO3 was more than 11 equivalents, the 2-substituted benzimidazole could be highly selectively formed as the sole product. NaHSO3 was firstly reacted with aldehyde to form the aldehyde sodium bisulfite, which reacted with o-phenylenediamine to form the 2-substituted benzimidazole and inhibited the formation of 1,2-disubstituted benzimidazole. This protocol solved the poor selectivity problem appearing in traditional method when cyclocondensation between o-phenylenediamine and aldehydes. The method also had advantage of simple work up by filtrating the single 2-substituted benzimidazole precipitates from reaction mixture at the end of the reaction without further purification. In addition, the method was applicable to both electron-rich and electron-poor starting materials, which was successfully used for synthesizing nine novel 2-substituted benzimidazole derivatives containing a 1,2,3-triazole moiety. They were characterized by NMR, IR and HRMS spectrum. Moreover, this method had been applied to a large scale synthesis of 2-substituted benzimidazole derivatives.