Copper-Catalyzed Aerobic Oxidative Amidation of Benzyl Alcohols
| العنوان: | Copper-Catalyzed Aerobic Oxidative Amidation of Benzyl Alcohols |
|---|---|
| المؤلفون: | Scott W. Krabbe, Vincent S. Chan, Thaddeus S. Franczyk, Justin A. Simanis, Carmina A. Presto, Shashank Shekhar, José G. Napolitano |
| المصدر: | The Journal of Organic Chemistry. 81:10688-10697 |
| بيانات النشر: | American Chemical Society (ACS), 2016. |
| سنة النشر: | 2016 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Base (chemistry), 010405 organic chemistry, ved/biology, Organic Chemistry, ved/biology.organism_classification_rank.species, Hydrazine, chemistry.chemical_element, Alcohol, Oxidative phosphorylation, 010402 general chemistry, 01 natural sciences, Oxygen, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Organic chemistry, Reactivity (chemistry), Amine gas treating, Conjugate acid |
| الوصف: | A Cu-catalyzed synthesis of amides from alcohols and secondary amines using the oxygen in air as the terminal oxidant has been developed. The methodology is operationally simple requiring no high pressure equipment or handling of pure oxygen. The commercially available, nonprecious metal catalyst, Cu(phen)Cl2, in conjunction with di-tert-butyl hydrazine dicarboxylate and an inorganic base provides a variety of benzamides in moderate to excellent yields. The pKa of amine conjugate acid and electronics of alcohol were shown to impact the selection of base for optimal reactivity. A mechanism consistent with the observed reactivity trends, KIE, and Hammett study is proposed. |
| تدمد: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.6b01686 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::79a1ca5fef51f9371f4f2726fd1fbb0c https://doi.org/10.1021/acs.joc.6b01686 |
| رقم الانضمام: | edsair.doi.dedup.....79a1ca5fef51f9371f4f2726fd1fbb0c |
| قاعدة البيانات: | OpenAIRE |
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