Xiao-Ling Liu

Efficient Friedländer Synthesis of Quinoline Derivatives from 2-Aminoarylketones and Carbonyl Compounds Mediated by Recyclable PEG-Supported Sulfonic Acid

Abstract 2-Aminoarylketones undergo smooth condensation with α-methylene ketones in the presence of 10 mol% of poly(ethylene glycol) (PEG)–supported sulfonic acid under mild reaction conditions to afford the corresponding poly-substituted quinolines in excellent yields. The catalyst can be recovered by simple filtration and can be recycled in subsequent reactions. The method is simple, cost-effective, and environmentally benign.

Selenium-Linking Strategy for Traceless Solid-Phase Synthesis of Acrylamides

Abstract A novel polystyrene-supported β-selenopropionic acid has been developed and applied to simple and efficient synthesis of acrylamides.

PEG-SUPPORTED SULFONIC ACID AS AN EFFICIENT AND RECYCLABLE CATALYST FOR THE SYNTHESIS OF 1,1-DIACETATES UNDER SOLVENT-FREE CONDITIONS

Abstract An operationally simple, efficient, and environmentally benign synthesis of 1,1‐diacetates in good yields by reaction of different aldehydes with acetic anhydride in the presence of PEG‐supported sulfonic acid under solvent‐free conditions is described.

A convenient selenium-linking strategy for traceless solid-phase synthesis of diethyl 1-alkenephosphonates

Abstract Treatment of a novel polymer‐supported α‐diethoxyphosphoryl methyl selenide with LDA followed by alkylation and oxidative deselenation efficiently afforded diethyl trans‐1‐alkenephosphonates in good yields and purities.

Novel Traceless Liquid‐Phase Synthesis of Coumarin Derivatives on Poly(Ethylene Glycol) Support

Abstract Coumarin derivatives were prepared by the von Pechmann reaction of PEG‐bound acetoacetate reagent with phenols in the presence of TiCl4 in excellent yield and purity with a facile workup procedure. The polymer reagent could be recycled two to four times without diminishing the yield or purity.

Facile Solid‐Phase Synthesis of Cycloalkylphosphonates and 1‐Cycloalkenylphosphonates Using Polymer‐Supported Phenylsulfonylmethylphosphonates

Abstract A facile procedure for the solid‐phase synthesis of cycloalkylphosphonates and 1‐cycloalkenylphosphonates in good yields and high purities using polystyrene‐supported phenylsulfonylmethylphosphonates with traceless sulfone linker strategy is described.

Synthesis and characterization of new poly(aryl ether ketone)s bearing (4-phenoxyphenyl)triphenylmethane moieties

1,1-Bis(4-hydroxyphenyl)-1-(4-phenoxyphenyl)-1-phenylmethane (BHPPPPM), a new bisphenol monomer, was synthesized with 65% yield from 4-benzoyl diphenyl ether in a one-pot, two-step synthetic procedure. Four new poly(aryl ether ketone)s (PAEKs) bearing (4-phenoxyphenyl)triphenylmethane moieties were prepared from BHPPPPM with four difluorinated aromatic ketones via a nucleophilic substitution reaction. The polycondensation proceeded in tetramethylene sulfone in the presence of anhydrous potassium carbonate and afforded the new PAEKs in nearly quantitative yields with inherent viscosities of 0.60–0.78 dL g−1. The resulting PAEKs having number-average molecular weights in the range of 29,500–34,200 g mol−1 with the polydispersity index ranged from 1.94 to 2.01 are all amorphous and show high glass transition temperatures ranging from 174°C to 196°C, excellent thermal stability, and the temperatures at the 5% weight loss are over 500°C with char yields above 60% at 700°C under nitrogen atmosphere. These new PAEKs are all soluble in polar aprotic solvents such as N-methyl-2-pyrrolidone and N,N′-dimethylacetamide and could also be dissolved in chloroform and tetrahydrofuran. All the polymers formed transparent, strong, and flexible films with tensile strengths of 78–85 MPa, tensile moduli of 1.9–2.4 GPa, and elongations at break of 7–10%.

Liquid-Phase Organic Synthesis of Thiazoles Using Poly(ethylene glycol)–Bound Sulfonyl Chloride Resin

Abstract Reaction of poly(ethylene glycol) (PEG)–bound sulfonic acid with thionyl chloride formed difunctionalized PEG-bound sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with thioamides in the presence of potassium carbonate, to afford thiazoles in good yields with a facile workup procedure.

Rapid Microwave‐Assisted Liquid‐Phase Synthesis of 4‐Substituted‐5‐methoxycarbonyl‐6‐methyl‐3,4‐dihydropyridones on Poly(ethylene Glycol) Support

Abstract 4‐Substituted‐5‐methoxycarbonyl‐6‐methyl‐3,4‐dihydropyridones have been efficiently prepared on the soluble polymer polyethylene glycol (PEG) 4000 by solvent‐free microwave irradiation through a one‐pot condensation of PEG‐bound acetoacetate, Meldrums acid, ammonium acetate, and the appropriate aldehyde in the presence of a catalytic amount of polyphosphoric acid. The polymer‐supported synthesis provided the target compounds in excellent yield and purity with a facile workup procedure.

Facile One‐Pot Synthesis of Oxazolidin‐2‐ones from Phenyl 2‐Hydroxyalkyl Selenides

Abstract A novel, convenient, efficient, three‐step, one‐pot synthesis of 2‐oxazolidinones from phenyl 2‐hydroxyalkyl selenides was developed. Using this methodology, 2‐oxazolidinones are obtained in good yields (76–85%) by reaction of phenyl 2‐hydroxyalkyl selenides with benzoyl isocyanate and subsequent oxidation/cyclization, followed by hydrolysis with hydrochloric acid solution.