Atom-Economical Palladium Carbon-Catalyzed de Novo Synthesis of Trisubstituted Nicotinonitriles
| Autor(en): | Sarkar, Debayan Rout, Nilendri Ghosh, Manoj Kumar Giri, Santanab Neue, Kornelius Reuter, Hans |
Stichwörter: | 1,3,5-TRISUBSTITUTED PYRAZOLINES; BOND FUNCTIONALIZATION; C-H ACTIVATION; Chemistry; Chemistry, Organic; HANTZSCH 1,4-DIHYDROPYRIDINES; METALATED PYRIDINES; ONE-POT SYNTHESIS; OXIDATIVE AROMATIZATION; ROOM-TEMPERATURE; SUBSTITUTED PYRIDINES; TITANIUM(II) ALKOXIDE | Erscheinungsdatum: | 2017 | Herausgeber: | AMER CHEMICAL SOC | Journal: | JOURNAL OF ORGANIC CHEMISTRY | Volumen: | 82 | Ausgabe: | 17 | Startseite: | 9012 | Seitenende: | 9022 | Zusammenfassung: | A de novo palladium carbon-catalyzed synthesis of trisubstituted nicotinonitriles from easily synthesized homopropagylic or homoallylic aromatic alcohols in the presence of nitriles has been explored. The mechanism proceeds with an interesting generation of a Pd(II)-C palladacycle followed by an oxidative aromatization to generate the pyridine core. The pyridine core is generated with a noteworthy C-C bond cleavage in the case of the substituted nitriles. The moderate yields and easy separation of the products lend a unique importance to this one-pot methodology |
ISSN: | 00223263 | DOI: | 10.1021/acs.joc.7b01332 |
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