通过卤素原子转移介导的可持续光诱导脱羧氯化反应
Sustainable Photoinduced Decarboxylative Chlorination Mediated by Halogen Atom Transfer.
作者信息
Levitre Guillaume, Granados Albert, Molander Gary A
机构信息
Department of Chemistry, University of Pennsylvania, Roy and Diana Vagelos Laboratories 231 S. 34th Street, Philadelphia, PA 19104-6323 (USA).
出版信息
Green Chem. 2023 Jan 21;25(2):560-565. doi: 10.1039/d2gc04578h. Epub 2023 Jan 6.
Abstract
Chlorinated organic backbones constitute important components in existing biologically active chemicals, and they are extraordinary useful intermediates in organic synthesis. Herein, an operationally simple and sustainable halodecarboxylation protocol halogen-atom transfer (XAT) as a key step is presented. The method merges a metal-free photoredox system with (diacetoxyiodo)benzene (PIDA) as a hypervalent iodine reagent using 1,2-dihaloethanes as halogen sources to afford haloalkanes in an efficient manner. The sustainability of this protocol is highlighted by an important waste recovery protocol as well as by atom economy and carbon efficiency parameters.
摘要
氯化有机骨架是现有生物活性化学品的重要组成部分，也是有机合成中极为有用的中间体。本文介绍了一种操作简单且可持续的卤代脱羧反应方案，该方案以卤原子转移（XAT）为关键步骤。该方法将无金属光氧化还原体系与作为高价碘试剂的（二乙酰氧基碘）苯（PIDA）相结合，使用1,2 - 二卤乙烷作为卤素源，以高效的方式制备卤代烷烃。该方案的可持续性通过重要的废物回收方案以及原子经济性和碳效率参数得以体现。
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