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一种使用二硫代氨基甲酸盐阴离子催化的可见光介导的三组分自由基过程。

A visible-light mediated three-component radical process using dithiocarbamate anion catalysis.

作者信息

Cuadros Sara, Horwitz Matthew A, Schweitzer-Chaput Bertrand, Melchiorre Paolo

机构信息

ICIQ - Institute of Chemical Research of Catalonia , The Barcelona Institute of Science and Technology , Avenida Països Catalans 16 , 43007 , Tarragona , Spain . Email:

IIT - Istituto Italiano di Tecnologia , Laboratory of Asymmetric Catalysis and Photochemistry , Via Morego 30 , 16163 , Genoa , Italy.

出版信息

Chem Sci. 2019 Apr 30;10(21):5484-5488. doi: 10.1039/c9sc00833k. eCollection 2019 Jun 7.

Abstract

We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals an S2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell intermediates from substrates that would be incompatible with or inert to classical radical-generating strategies. The redox-neutral conditions of this process make it tolerant of redox-sensitive substrates and allow the installation of multiple biologically relevant heterocycles within the cascade products.

摘要

我们报道了一种光诱导的三组分自由基过程,该过程能使易得的烷基氯化物、马来酰亚胺和杂芳族片段快速偶联,以高非对映选择性快速生成复杂的手性产物。该方法通过基于S2的光化学催化机制产生自由基,不依赖于前体的氧化还原性质。因此,它能从与经典自由基生成策略不相容或呈惰性的底物中获得开壳中间体。该过程的氧化还原中性条件使其能耐受氧化还原敏感的底物,并允许在级联产物中安装多个具有生物学相关性的杂环。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b198/6553376/98fe45957f69/c9sc00833k-f1.jpg

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