10.1016/S0040-4039(02)01755-0
The research focuses on the development of an efficient and recyclable method for the preparation of benzhydryl ethers, a common protective group for alcohols in organic synthesis. The study utilizes Nafion-H, a perfluorinated sulfonic acid resin, as a solid acid catalyst for this purpose. The experiments involved mixing alcohol and diphenylmethanol in the presence of a catalytic amount of Nafion-H in acetonitrile at 80°C, optimizing the solvent, reaction temperature, and catalyst to substrate ratio. The reaction yield was found to be highest in acetonitrile, with primary alcohols being more reactive than secondary and tertiary alcohols. The method was extended to various hydroxyl compounds, and the results were summarized in a table, showing high yields for benzylic and primary alcohols with minimal formation of dibenzhydryl ether. The catalyst's recyclability was tested over eight reaction cycles without significant loss of activity. The products were analyzed using column chromatography, gas chromatography (GC), and proton nuclear magnetic resonance (1H NMR) to confirm their structures.
10.1016/j.tetlet.2012.02.011
The research investigates an efficient method for synthesizing diphenylmethyl ethers and thioethers using microwave irradiation and protic ionic liquids (pILs) as co-solvent and catalyst. The study optimizes reaction conditions, identifying TeaMs (triethylamine-methane sulfonic acid) as the most effective pIL for the formation of diphenylmethyl ethers from diphenylmethanol and various alcohols, achieving high yields (60–98%) in short reaction times (10–30 minutes) under mild conditions (80°C). The methodology was also successfully applied to the synthesis of thioethers. Key chemicals involved in the research include diphenylmethanol, various alcohols (such as ethanol, methanol, and n-propanol), protic ionic liquids (TeaH2SO4, TeaMs, TeaFM, and TeaTFA), and thiol compounds (1-octanethiol and thiophenol). The use of microwave irradiation and pILs provides a rapid and clean approach to installing diphenylmethyl groups, offering a practical alternative to traditional methods and demonstrating potential for further synthetic applications.