Visible Light-Mediated (Hetero)aryl Amination Using Ni(II) Salts and Photoredox Catalysis in Flow: A Synthesis of Tetracaine
| العنوان: | Visible Light-Mediated (Hetero)aryl Amination Using Ni(II) Salts and Photoredox Catalysis in Flow: A Synthesis of Tetracaine |
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| المؤلفون: | Stephen L. Buchwald, Michael T. Pirnot, Boyoung Y Park |
| المصدر: | The Journal of Organic Chemistry. 85:3234-3244 |
| بيانات النشر: | American Chemical Society (ACS), 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | Light, 010405 organic chemistry, Aryl, Organic Chemistry, Halide, Substrate (chemistry), chemistry.chemical_element, Photoredox catalysis, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, Nickel, chemistry.chemical_compound, Tetracaine, chemistry, Yield (chemistry), Salts, Amine gas treating, Amination |
| الوصف: | We report a visible light-mediated flow process for C-N cross-coupling of (hetero)aryl halides with a variety of amine coupling partners through the use of a photoredox/nickel dual catalyst system. Compared to the method in batch, this flow process enables a broader substrate scope, including less-activated (hetero)aryl bromides and electron-deficient (hetero)aryl chlorides, and significantly reduced reaction times (10 to 100 min). Furthermore, scale up of the reaction, demonstrated through the synthesis of tetracaine, is easily achieved, delivering the C-N cross-coupled products in consistently high yield of 84% on up to a 10 mmol scale. |
| تدمد: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.9b03107 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::da87dfd197d02a2bb94daffb0583e4e2 https://doi.org/10.1021/acs.joc.9b03107 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....da87dfd197d02a2bb94daffb0583e4e2 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15206904 00223263 |
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| DOI: | 10.1021/acs.joc.9b03107 |