通过卤素α-亲核加成光催化缺电子烯烃的三组分二氟烷基卤化。

IF 3.7 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - A European Journal Pub Date : 2025-03-12 DOI:10.1002/chem.202500434

Xiaoxiao Liu, Di Chao, Qingfeng Liu, Yingchao Ma, Zhiguo Zhang, Tongxin Liu, Xingjie Zhang, Prof. Guisheng Zhang

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引用次数: 0

摘要

在这里，我们揭示了一个卤素α-亲核加成，通过光催化氧化原位生成的酰胺或酯的α-羰基自由基到相应的α-羰基阳离子。α-碳自由基是由BrCF2CO2R光催化还原形成的二氟烷基自由基β加成到α，β-不饱和酰胺/酯上生成的。这种混合策略使α、β-不饱和酰胺或酯与BrCF2CO2R和Cl/ f亲核试剂进行有效的三组分二氟烷基卤化反应，在温和的条件下产生多种具有重要生物学意义的含cf2的α-卤-1,5-二羧基衍生物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Photocatalyzed Three-Component Difluoroalkyl-Halogenation of Electron-Deficient Alkenes via a Halogen α-Nucleophilic Addition

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Photocatalyzed Three-Component Difluoroalkyl-Halogenation of Electron-Deficient Alkenes via a Halogen α-Nucleophilic Addition

Here, we disclose a halogen α-nucleophilic addition via photocatalytic oxidation of the in-situ generated α-carbonyl radical of amides or esters to corresponding α-carbonyl cation. The α-carbon radical is generated by the β-addition of difluoroalkyl radical, formed by the photocatalytic reduction of BrCF₂CO₂R, to the α,β-unsaturated amides/esters. This umpolung strategy enables an efficient three-component difluoroalkyl-halogenation of α,β-unsaturated amides or esters with BrCF₂CO₂R and Cl/F-nucleophiles to produce diverse biologically important CF₂-containing α-halo-1,5-dicarboxylic derivatives under mild conditions.

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来源期刊

Chemistry - A European Journal 化学-化学综合

CiteScore

7.90

自引率

4.70%

发文量

1808

审稿时长

1.8 months

期刊介绍： Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields. Based in Europe Chemistry—A European Journal provides an excellent platform for increasing the visibility of European chemistry as well as for featuring the best research from authors from around the world. All manuscripts are peer-reviewed, and electronic processing ensures accurate reproduction of text and data, plus short publication times. The Concepts section provides nonspecialist readers with a useful conceptual guide to unfamiliar areas and experts with new angles on familiar problems. Chemistry—A European Journal is published on behalf of ChemPubSoc Europe, a group of 16 national chemical societies from within Europe, and supported by the Asian Chemical Editorial Societies. The ChemPubSoc Europe family comprises: Angewandte Chemie, Chemistry—A European Journal, European Journal of Organic Chemistry, European Journal of Inorganic Chemistry, ChemPhysChem, ChemBioChem, ChemMedChem, ChemCatChem, ChemSusChem, ChemPlusChem, ChemElectroChem, and ChemistryOpen.