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Catalysts · 2023 ·Vol. 13 ·期 4 ·726 · IF 3.9

Heterogeneous Chitosan@copper Catalyzed Selective C(sp3)–H Sulfonylation of Ketone Hydrazones with Sodium Sulfinates: Direct Access to β-Ketosulfones

Jun Qiao,Kai Zheng,Zhiwei Lin,Huiye Jin,Wenbo Yu,Chao Shen,Aiquan Jia,Qianfeng Zhang

The exploration of inexpensive and stable heterogeneous catalysts for C–S coupling reactions remains a challenging issue. Herein, we successfully prepared a new biomass-derived copper catalyst and applied it to the selective C(sp3)–H-directed sulfonylation of ketone hydrazones with commercial sodium sulfinates. The catalyst was characterized using different spectroscopic and microscopic techniques. Importantly, the prepared biomass-supported Cu catalyst catalyzed the C–S coupling reaction with considerably high activity. A variety of aryl and alkyl sulfinates were converted to the corresponding sulfones with good yields. In particular, the heterogeneous catalyst could be recovered easily after the synthesis and consecutively used at least five times with no appreciable decrease in the catalytic activity. Lastly, the copper catalyst is expected to have further applications in organic reactions catalyzed by Cu/CuO2.Keywords:biomass-derived;copper catalysts;heterogeneous;C–S coupling

CAS / MDL: 9012-76-4
研究领域: 有机化学 · 催化化学
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TETRAHEDRON LETTERS · 2020 · IF 2.275

Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates

Youming Huang,Hongyi Chen,Wenting Zheng,Qingle Zeng

A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu 2 O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu 2 O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).

CAS / MDL: 2627-86-3 3886-69-9
研究领域: 有机化学 · 合成化学
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NEW JOURNAL OF CHEMISTRY · 2018 ·Vol. 42 ·期 19 ·16013-16020 · IF 3.201

Efficient Ullmann C–X coupling reaction catalyzed by a recoverable functionalized-chitosan supported copper complex

Xuemin Liu,Shuo Chang,Xinzhi Chen,Xin Ge,Chao Qian

Three different types of functionalized-CS were prepared and anchored with copper salts for use as the catalyst for the Ullmann C–X coupling reaction. The Schiff-basic chitosan supported copper complex (PCCS@CuI) exhibits the highest catalytic activity. The structure of the catalyst was characterized by FTIR spectroscopy, TG, XRD, SEM, EDS and XPS. This catalyst exhibited high applicability for the C–N and C–S coupling reactions, in which good to excellent yields were obtained. Its easy separation, good reusability and stability were notable.

CAS / MDL: 9012-76-4
研究领域: 有机化学 · 材料科学
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GREEN CHEMISTRY · 2014 ·Vol. 16 ·期 6 ·3007-3012 · IF 6.852

A highly active and easily recoverable chitosan@copper catalyst for the C–S coupling and its application in the synthesis of zolimidine

Chao Shen,Jun Xu,Wenbo Yu,Pengfei Zhang

Aryl sulfones were synthesized using a highly active and easily recoverable heterogeneous Cu catalyst which was prepared by simply stirring an aqueous suspension of chitosan in water with copper salts. The chitosan@copper catalyst catalyzed the coupling reactions of aryl halides with sodium sulfinates to readily give the corresponding sulfones in good to excellent yields. The highly active catalyst can be reused many times without losing its catalytic activity. In addition, by using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily.

CAS / MDL: 9012-76-4
研究领域: 有机化学 · 药物合成
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Tandem micellar catalysis and cloud point extraction process for C-S coupling reaction in water

Xin Ge,Weili Song,Xinzhi Chen,Chao Qian,Shaodong Zhou,Xuemin Liu

A tandem process of micellar catalysis and cloud point extraction (CPE) is developed for copper-catalyzed Ullmann C-S coupling reactions in water. The functional nonionic surfactant, amine terminated polyether M2070, affords nano-micelle environment in the aqueous system; the latter splits to two phases above the cloud point temperature (CPT). The nature of the micellar catalysis in M2070 aqueous was investigated by DLS, EDS, XPS, IR, TEM and 1 H NMR. M2070 was verified to provide nano-space for encapsulation and aggregation of the substrates. More importantly, the metallic micelle formed by M2070 chelating copper was identified. It is noteworthy that excellent productivity in pre-micellar catalysis of C-S coupling reactions was obtained with good tolerance of substrate. Finally, the water-micelle system was separated into two phases above the CPT thus to achieve the product separation. Furthermore, the M2070/water system can be recycled and reused.

研究领域: 化学工程 · 催化化学
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JOURNAL OF ORGANIC CHEMISTRY · 2025 · IF 3.6

Synthesis of Thienoacenes via Cascade Copper-Catalyzed C–S Coupling and Thienannulation Reactions and Their Thermoelectric Properties

Jiaxuan Dong,Yifan Lv,Yiyang Li,Kexin Xu,Xinrui Cui,Cun-Yue Guo,Baolin Li

Thienoacenes are a prominent class of fused-ring conjugated organic compounds and have attracted considerable attention due to their high coplanarity, good stability, high charge-carrier mobility, etc. However, most current synthetic methods toward thienoacenes require costly starting materials and reagents, as well as a lengthy synthetic procedure with low overall yields. Herein, a nonprecious copper-catalyzed system without additional ligands was developed to facilitate C–S coupling and 5-endo-dig thienannulation reaction, leading to the synthesis of a range of thienoacenes including dithieno[3,2-b:2′,3′-d]thiophenes (DTTs) and thieno[2′,3′:4,5]thieno[3,2-b]thiophene[2,3-d]thiophene (TTAs) with yields of up to 90% (for single-sided thienannulation reactions) and 65% (for double-sided thienannulation reactions). In addition, three π-extended DTTs were studied as potential thermoelectric materials, and their composites with single-walled carbon nanotubes (SWCNTs) exhibited high thermoelectric performance with the power factor up to 399.01 ± 16.26 μW m–1 K–2 at room temperature, which is the highest reported for thermoelectric composites comprising small-molecule thiophene derivatives and SWCNTs, signifying a step forward in the development of high-performance thermoelectric composites based on thiophene derivatives.

研究领域: 有机化学 · 材料科学 · 热电研究
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