Center for Bioinformatics and Molecular Medicine, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan.
Department of Pharmaceutical Organic Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo, Nagasaki 852-8521, Japan.
J Org Chem. 2021 Dec 17;86(24):18017-18029. doi: 10.1021/acs.joc.1c02316. Epub 2021 Dec 2.
General methods have not been previously developed for the synthesis of sterically hindered α-SCF-substituted carbonyl compounds using nucleophilic trifluoromethylthiolating reagents. Thus, we herein report spC-SCF bond formation in hindered α-bromoamides containing 3-bromo-oxindoles and linear α-bromoamides using CuSCF or AgSCF under mild conditions to access sterically hindered α-SCF-substituted amides. This transformation is applicable to not only 3-SCF-substituted oxindoles but also primary and secondary amides and reveals a broad functional group tolerance. This method will benefit the fields of medicinal and agricultural chemistry.
先前尚未开发出使用亲核三氟甲基硫代试剂合成空间位阻α-SCF 取代羰基化合物的一般方法。因此，我们在此报告了使用 CuSCF 或 AgSCF 在温和条件下，通过含有 3-溴吲哚啉和线性α-溴酰胺的受阻α-溴酰胺形成 spC-SCF 键，以获得空间位阻α-SCF 取代酰胺。这种转化不仅适用于 3-SCF 取代的吲哚啉，还适用于伯酰胺和仲酰胺，并且显示出广泛的官能团耐受性。该方法将有益于医药和农业化学领域。
