Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o-hydroxyaryl enaminones.

We herein propose a HFIP-promoted tandem cyclization reaction for the synthesis of difluoro/trifluoromethyl carbinol-containing chromones from o-hydroxyphenyl enaminones at room temperature. This protocol provides a facile and efficient approach to access diverse difluoro/trifluoromethylated carbinols in good to excellent yields. In addition, gram-scale and synthetic derivatization experiments have also been performed.

1,1,1,3,3,3-Hexafluoro-2-Propanol-Promoted Friedel-Crafts Reaction: Metal-Free Synthesis of C3-Difluoromethyl Carbinol-Containing Imidazo[1,2-a]pyridines at Room Temperature.

A facile and efficient method has been developed for the synthesis of C3-difluoromethyl carbinol-containing imidazo[1,2-a]pyridines at room temperature via the HFIP-promoted Friedel-Crafts reaction of difluoroacetaldehyde ethyl hemiacetal and imidazo[1,2-a]pyridines. This strategy could be applied to the direct C(sp2)-H hydroxydifluoromethylation of imidazo[1,2-a]pyridines and afford a series of novel difluoromethylated carbinols in good to satisfactory yields with 29 examples. Furthermore, gram-scale and synthetic transformation experiments have also been achieved, demonstrating its potential applicable value in organic synthesis. This green protocol has several advantages, including being transition metal- and oxidant-free, being carried out at room temperature, having high efficiency, and having a wide substrate scope.

Robust superhydrophobic and superoleophilic filter paper via atom transfer radical polymerization for oil/water separation.

Robust superhydrophobic and superoleophilic cellulose-g-PFOEMA filter paper membranes were fabricated via surface grafting of poly(perfluorooctylethyl methacrylate) (PFOEMA) using atom transfer radical polymerization (ATRP). The surface chemical compositions, morphologies and wettability of cellulose-g-PFOEMA with different degree of graft ratio (DG) were investigated using attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR), X-ray photoelectron spectroscopy (XPS), scanning electron microscope (SEM), and contact angle (CA) measurement. IR and XPS showed that PFOEMA were introduced into surface of filter paper. The superhydrophobicity of filter paper increased with amount of PFOEMA grafted. When DG of grafted PFOEMA was higher than 11.2%, the superhydrophobicity reached a steady state and the measured water contact angle was about 157°. The PFOEMA-grafted filter paper exhibited excellent chemical resistance toward a wide range of pH solution from 1 to 12. Cellulose-g-PFOEMA is convenient for oil/water separation with efficiency higher than 95%. The excellent reusability and stability make cellulose-g-PFOEMA filter paper membrane a promising candidate in the applications of oil spillage cleanup and the separation of oil/water mixture.