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APPLIED ORGANOMETALLIC CHEMISTRY · 2014 ·Vol. 28 ·期 8 ·635-640 · IF 2.017

β-cyclodextrin-capped palladium nanoparticle-catalyzed ligand-free Suzuki and Heck couplings in low-melting β-cyclodextrin/NMU mixtures

Xiaohua Zhao,Xiang Liu,Ming Lu

Low-melting β-cyclodextrin/ N -methylurea (NMU) mixture, an efficient catalytic system for ligand-free Suzuki and Heck couplings in the presence of fresh native β-CD-capped Pd 0 nanoparticles, has been successfully reported. This natural and convenient system can be performed in air and could afford the corresponding cross-coupled products in good to excellent isolated yields after a simple workup under every low Pd loading (0.05 mol%). Remarkably, the catalytic system can be recycled and reused without loss of catalytic activity. Copyright © 2014 John Wiley & Sons, Ltd.

CAS / MDL: 7585-39-9 598-50-5
研究领域: 化学 · 材料科学 · 催化反应
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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

Palladium nanoparticles immobilized on N-decorated porous carbon as synergistic catalyst for carbon-carbon coupling reactions

Bin Zhao,Ningzhao Shang,Shutao Gao,Chun Wang

N -decorated porous carbon (NDC) was obtained by one step direct pyrolysis of NH 2 -MIL-125. The content of nitrogen in the NDC-1000 (2 h) was 4.2%. Palladium nanoparticle was deposited on the NDC by an impregnation strategy. The NDC-1000-Pd catalyst was characterized by powder X-ray diffraction, TEM, XPS and N 2 adsorption. Due to the synergetic interaction of metal species and NDC, the catalyst exhibited excellent catalytic performance for Heck coupling and Suzuki-Miyaura reactions. The catalyst can be reused for five cycles without obvious change in its activity.

研究领域: 化学催化 · 材料科学
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E-POLYMERS · 2020 ·Vol. 20 ·期 1 ·16-31 · IF 1.675

Novel benzimidazole-based conjugated polyelectrolytes: synthesis, solution photophysics and fluorescent sensing of metal ions

Yuhan Wei,Lei Xu,Shengjiao He,Chenglei Li,Qi Wu,Xianyin Zeng,Hanguang Wang,Kuan Liu

Two benzimidazole-based conjugated polyelectrolytes (+)-PPBIPV and (-)-PPBIPV which have opposite charges on their side chains were synthesized via Heck coupling reaction and characterized by 1 H-NMR, UV-vis and PL spectroscopy. These two polyelectrolytes are both consisted of benzimidazole derivatives and phenylenevinylene units. The absorption and emission spectra reveal that the polymers both have solvent-dependency and concentration-dependency, and they exhibit aggregation effect in aqueous solution. In the respect of ion detection, the aqueous solution of (+)-PPBIPV has excellent selectivity and sensitivity for Fe 3+ . Moreover, Pd 2+ can almost completely quench the fluorescence of (+)-PPBIPV in methanol solution, and its quenching constant K SV is 5.93×10 4 M -1 . For (-)-PPBIPV, Sn 2+ can double the fluorescence intensity of its aqueous solution, while (-)-PPBIPV has good identification for Fe 3+ in methanol with a K SV = 3.44×10 5 M -1 . Hence, two polyelectrolytes have considerable potential to become effective fluorescent sensing materials for some specific metal ions. All of the stoichiometric relationships between metal ions and conjugated polyelectrolytes were calculated using Benesi-Hildebrand equation.

研究领域: 材料化学 · 分析化学
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ORGANIC & BIOMOLECULAR CHEMISTRY · 2022 ·Vol. 20 ·期 14 ·2909-2921 · IF 3.89

Asymmetric total synthesis of (+)-(2R,4′R,8′R)-α-tocopherol enabled by enzymatic desymmetrization

Haidi Yang,Jinyao Liu,Pan Hu,Liang Gao,Zedu Huang,Fener Chen

A new and highly stereoselective synthesis of chiral diol (S)-14, the common synthetic intermediate to (+)-(2R,4′R,8′R)-α-tocopherol (1), was accomplished in seven steps with 13.8% overall yield. This developed route featured a lipase-catalyzed desymmetric hydrolysis of prochiral diester 39a, which was prepared through a challenging Heck coupling, to chiral quaternary carbon-containing monoester (R)-37a of the correct configuration in 81% yield and 96.7% ee, to the best of our knowledge, leading to the most efficient enzymatic desymmetric synthesis of the chiral chroman skeleton of vitamin E members reported to date. Coupled with the modified preparation of the phytol-derived side chain, the chemoenzymatic total synthesis of 1 was completed in 15 longest linear steps with 3.1% overall yield.

研究领域: 有机化学 · 合成化学 · 酶学
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KINETICS AND CATALYSIS · 2013 ·Vol. 54 ·期 6 ·716-723 · IF 0.543

Preparation of a novel CuI/PCMS heterogeneous catalyst for Heck-type cross-coupling reactions

Zeng Minfeng,Sun Xudong,Qi Chenze,Zhang Xian-Man

A novel and environmentally friendly heterogeneous catalyst has been prepared through the wet impregnation of copper(I) species onto the highly porous chitosan microspheres (CuI/PCMS). This novel CuI/PCMS heterogeneous catalyst with no additional ligands is much better than CuI homogeneous catalysts when applied in Heck reactions. Moreover, the reaction conditions are much milder than those for the similar copper catalysts mediated cross-coupling reactions reported in the literature. PCMS has been demonstrated not only the excellent solid support, but also have many unique functional groups to chelate the copper (I) species to enhance its catalytic activity.

研究领域: 催化化学 · 有机合成 · 材料化学 · 环境友好化学 · 功能高分子材料
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Polymer Chemistry · 2015 ·Vol. 6 ·期 35 ·6351-6357 · IF 5.52

One-pot approach to Pd-loaded porous polymers with properties tunable by the oxidation state of the phosphorus core

Xiaoyu Jiang,Wuxue Zhao,Wei Wang,Fan Zhang,Xiaodong Zhuang,Sheng Han,Xinliang Feng

Two novel Pd-loaded heteroatom-linked microporous polymers Pd@NP and Pd@NPO were effectively synthesized by one-pot Pd-catalyzed Heck coupling reactions of tris(4-vinylphenyl)amine with tris(4-bromophenyl)phosphine and tris(4-bromophenyl)phosphine oxide, respectively. The Pd atoms loaded into the networks of the resulting porous polymers originated from the Pd-catalyst used in the polymerization, which was achieved under moderate reaction conditions. Besides the nitrogen atoms, the trivalent phosphorus atoms bearing one lone pair of electrons and the pentavalent phosphorus atoms of the phosphoryl groups were used as the linkers for the formation of the frameworks of the porous polymers Pd@NP and Pd@NPO, respectively. The phosphorus atoms with different oxidation states in the networks caused a dramatic variation in the physical and catalytic properties of the as-prepared porous polymers. Pd@NP and Pd@NPO exhibit surface areas of 381 m2 g−1 and 684 m2 g−1, respectively. Both Pd-loaded porous polymers enable efficient Suzuki–Miyaura coupling reactions featuring short reaction times and good yields, with the catalysts being highly stable and easy to recycle. The catalytic activity of Pd@NPO is higher than that of Pd@NP.

研究领域: 材料化学 · 有机化学 · 催化化学 · 高分子科学 · 纳米功能材料
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