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Benzylic Fluorination of Aza‐Heterocycles Induced by Single‐Electron Transfer to Selectfluor
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-03-22 , DOI: 10.1002/anie.201801280
Kelley E Danahy 1 , Julian C Cooper 1 , Jeffrey F Van Humbeck 2
Affiliation  

A selective and mild method for the benzylic fluorination of aromatic azaheterocycles with Selectfluor is described. These reactions take place by a previously unreported mechanism, in which electron transfer from the heterocyclic substrate to the electrophilic fluorinating agent Selectfluor eventually yields a benzylic radical, thus leading to the desired C−F bond formation. This mechanism enables high intra‐ and intermolecular selectivity for aza‐heterocycles over other benzylic components with similar C−H bond‐dissociation energies.

中文翻译:

单电子转移至 Selectfluor 诱导氮杂杂环的苄基氟化

描述了一种使用 Selectfluor 对芳香氮杂杂环进行苄基氟化的选择性温和方法。这些反应通过以前未报道的机制发生,其中电子从杂环底物转移到亲电子氟化剂 Selectfluor 最终产生苄基自由基,从而导致所需的 CF 键形成。这种机制使氮杂杂环比具有相似 C-H 键解离能的其他苄基组分具有更高的分子内和分子间选择性。
更新日期:2018-03-22
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