التفاصيل البيبلوغرافية
| العنوان: |
Synthesis of Indolines via Base‐Mediated C−H Activation and Defluorinative C−N Coupling, with no Need for Transition‐Metals. |
| المؤلفون: |
Weindl, Christian, Hintermann, Lukas |
| المصدر: |
Chemistry - A European Journal; 7/2/2024, Vol. 30 Issue 37, p1-5, 5p |
| مصطلحات موضوعية: |
INDOLINE, CONDENSATION reactions, NATURAL products, IMINES, POTASSIUM, HETEROCYCLIC compounds, ANILINE, NITROGEN |
| مستخلص: |
Syntheses of (partially) aromatic nitrogen heterocycles increasingly rely on transition‐metal catalyzed C−C‐ and C−N‐cross‐coupling reactions. Here we describe a different approach to the synthesis of indolines by a domino C(sp3)−H activation, 1,2‐addition, and defluorinative SNAr‐cyclization sequence to provide the target 1,2‐diarylindolines (1,2‐diaryl‐2,3‐dihydroindoles) from ortho‐fluorinated methyl‐arenes and N‐aryl imines (benzylidene anilines) in a cyclocondensation that is mediated by potassium hexamethyldisilazide (KHMDS) as base exclusively. This transition‐metal‐free process via C−H and C−F bond activation provides a one‐step entry into a wide array of indoline scaffolds (43 examples, up to 96 % yield). This privileged substructure is common in natural products and pharmaceuticals alike, and cannot be accessed by traditional condensation reactions. [ABSTRACT FROM AUTHOR] |
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| قاعدة البيانات: |
Complementary Index |
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