Visible Light-Induced Diastereoselective Construction of Trifluoromethylated Cyclobutane Scaffolds through [2+2]-Photocycloaddition and Water-Assisted Hydrodebromination

作者：Xiao Hu, Weibo Xu, Yin Liu, Hao Guo · 发表于：The Journal of Organic Chemistry · 年份：2023 · DOI：10.1021/acs.joc.2c02976 · 被引用次数：30 · 研究领域：Fluorine in Organic Chemistry、Radical Photochemical Reactions、Catalytic C–H Functionalization Methods

A visible light-induced diastereoselective synthesis of trifluoromethylated cyclobutane derivatives is described, consisting of [2+2]-photocycloaddition and water-assisted hydrodebromination by one pot. Quinolinones, isoquinolinones, and coumarins are able to participate in this one-pot process with 1-bromo-1-trifluoromethylethene. In addition, stereodefined trisubstituted trifluoromethylated cyclobutane alcohols, carboxylic acids, and amines can be obtained in a straightforward manner through the ring opening of lactone or lactam without the loss of original high diastereoselectivity given by the water-tristrimethylsilylsilane coordination. The antineoplastic bioactivities of those compounds are also well studied, which exhibit great antineoplastic potential comparable to cisplatin. In the proposed mechanism, thioxanthone (TX) serves as a dual catalyst and a radical chain pathway may be involved in the hydrodebromination process.