Solid-phase Synthesis of Vinyl Ethers Based on Polystyrene-supported Phenyl 2-Hydroxyalkyl Selenide
【摘要】：正Vinyl ethers are valuable intermediates that can be used in a wide array of chemical transformations. Solution-phase synthetic methods for vinyl ethers are well documented. However, most of these methods involve drawbacks such as harsh reactions, laborious manipulation and low overall yields, or in some cases, reactions are unsuitable for sensitive substrates, vigorous toxic compounds are used or some reagents are not readily available. It is well known that phenylseleno group is readily converted to a leaving group thus giving access to carbon-carbon double bond via oxidation followed by β-elimination. However, organoselenium reagents always have a foul smell and are quite toxic, which is often problematic in organic synthesis. In connection with our interest in polymer-bound organoselenium reagents, which provided significant advantages, including decreased volatility and simplification of product work-up, we wish to report here a facile solid-phase synthetic approach to aryl vinyl ethers in good yields (70%-88%) and with high purities (95% byH NMR analysis) based on novel polymer-supported phenyl 2-hydroxyalkyl selenide.