Aryl thioglycosides have broad applicability as both glycosyl donors and glycomimetic compounds. Their synthesis via the cross-coupling of glycosyl thiols with aryl halides has become a popular method for their construction because it allows better selectivity for anomeric configuration as well as a wider functional group tolerance compared to traditional methods. Herein, we report a nickel-catalyzed method for the synthesis of aryl thioglycosides which utilizes an aqueous micellar environment as the reaction medium. This alternative method allows for mild conditions while circumventing expensive palladium, leading to the successful synthesis of over 30 aryl thioglycosides, including challenging 1,2-cis thioglycoside products.

中文翻译：

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一种在表面活性剂水溶液中用镍催化糖基硫醇烷基化反应的温和有效的方法


芳基硫代糖苷作为糖基供体和拟糖化合物具有广泛的适用性。它们通过糖基硫醇与芳基卤化物的交叉偶联合成已成为其构建方法的流行方法，因为与传统方法相比，它对异头构型具有更好的选择性以及更广泛的官能团耐受性。在此，我们报道了一种利用水性胶束环境作为反应介质合成芳基硫代糖苷的镍催化方法。这种替代方法允许在温和的条件下使用，同时避免了昂贵的钯，从而成功合成了 30 多种芳基硫代糖苷，包括具有挑战性的 1,2-顺式硫代糖苷产品。