Srinivasu Vinjamuri, Das Debabrata, Chandu Palasetty, Ghosh Krishna Gopal, Sureshkumar Devarajulu
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246, West Bengal, India.
Org Lett. 2023 Jul 21;25(28):5308-5313. doi: 10.1021/acs.orglett.3c01877. Epub 2023 Jul 7.
Trifluoromethyl bicyclo[1.1.1]pentanes (BCPs) have attracted significant attention from the scientific community and pharmaceutical industries due to their advantageous physicochemical properties as arene bioisosteres. Initial photoredox perfluoroalkylation of [1.1.1]propellane triggers the tandem reaction to the perfluoroalkyl BCP radical followed by Giese addition to an generated electron-deficient alkene by Knoevenagel condensation in a four-component fashion to form 1,3-functionalized BCPs. This strategy provides easy access to various 1,3-functionalized perfluoroalkyl BCP derivatives with the added advantage of nitrile group as a functional handle to diversified transformations. This methodology offers scalability and late-stage derivatization of drug molecules with high chemoselectivity.
三氟甲基双环[1.1.1]戊烷（BCPs）因其作为芳烃生物电子等排体的有利物理化学性质而受到科学界和制药行业的广泛关注。[1.1.1]螺桨烷的初始光氧化还原全氟烷基化引发串联反应生成全氟烷基BCP自由基，随后通过Knoevenagel缩合以四组分方式对生成的缺电子烯烃进行吉斯加成，形成1,3-官能化的BCPs。该策略提供了一种简便的方法来合成各种1,3-官能化的全氟烷基BCP衍生物，并且具有腈基作为官能团用于多样化转化的额外优势。这种方法具有可扩展性，并且能够以高化学选择性对药物分子进行后期衍生化。
