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光诱导 [2 + 2] 环加成反应构建环丁烷并吡啶基砜基氟化物。

Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides.

机构信息

State Key Laboratory of Silicate Materials for Architectures; School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, China.

出版信息

Org Biomol Chem. 2020 Jun 3;18(21):4019-4023. doi: 10.1039/d0ob00814a.

Abstract

Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.

摘要

环丁烷是一类重要的结构基序,存在于广泛的天然产物和其他具有重要生物学意义的分子中。通过吡啶酮或异喹啉酮与乙磺酰氟的光催化[2+2]环加成反应,提供了一类具有季刚性环的独特的环丁烷稠合的吡啶基磺酰氟(30 个实例)。这些新型磺酰氟分子在 SuFEx 点击化学中的进一步应用也得以实现,得到了相应的磺酸盐和磺酰胺,收率合理。

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