Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis 15771, Athens, Greece.
Center of Excellence for Drug Design and Discovery, National and Kapodistrian University of Athens, Panepistimiopolis 15771, Athens, Greece.
Org Biomol Chem. 2022 Jul 27;20(29):5836-5844. doi: 10.1039/d2ob01066f.
Sulfoxide-containing molecules are an important class of compounds in the pharmaceutical industry and many efforts have been made to develop new and green protocols, targeting the chemoselective transformation of sulfides into sulfoxides. Photochemistry is a rapidly expanding research field employing light as the energy source. Photochemical aerobic processes possess additional advantages to photochemistry and may find applications in the chemical industries. Herein, a 370 nm catalyst-free aerobic protocol was developed, using 2-Me-THF as the green solvent. At the same time, two low-catalyst-loading anthraquinone-based processes (under a CFL lamp or 427 nm irradiation) in 2-Me-THF were developed. Furthermore, a broad range of substrates was tested. We also implemented our protocols towards the synthesis of the pharmaceutical active ingredients (APIs) sulforaphane and modafinil.
含硫醚的分子是制药工业中一类重要的化合物，人们已经做出了许多努力来开发新的和绿色的方案，旨在将硫化物选择性转化为亚砜。光化学是一个快速发展的研究领域，它使用光作为能源。光化学有氧过程相对于光化学具有额外的优势，可能在化学工业中得到应用。在此，开发了一种在 370nm 下、以 2-Me-THF 为绿色溶剂、无需催化剂的有氧协议。同时，在 2-Me-THF 中开发了两种基于蒽醌的低催化剂负载的工艺（在 CFL 灯或 427nm 照射下）。此外，还对广泛的底物进行了测试。我们还将我们的方案应用于药物有效成分（APIs）萝卜硫素和莫达非尼的合成中。
