Beyond Click-Chemistry: Transformation of Azides with Cyclopentadienyl Ruthenium Complexes
| Autor: | Rosario Scopelliti, Kay Severin, Julie Risse |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
chemistry.chemical_element
Ligands Medicinal chemistry Coupling reaction Catalysis Inorganic Chemistry chemistry.chemical_compound Cyclopentadienyl complex Catalyzed Cycloaddition Tetrazene Organic chemistry Physical and Theoretical Chemistry Aldehydes Organic Chemistry Antiviral Activities Alkyne Cycloaddition Organic Azides Ruthenium Alpha-Aminophosphonate Moiety Benzonitrile Half-Sandwich Complexes chemistry Click chemistry Azide Derivatives Analogs |
| Zdroj: | Organometallics. 30:3412-3418 |
| ISSN: | 1520-6041 0276-7333 |
| Popis: | The cyclopentadienyl Ru complexes Cp*RuCl(cod) (cod = 1,5-cyclooctadiene), Cp*RuCl(PPh3)2, and [Cp∧RuCl2]2 (Cp∧ = η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl) are able to catalyze the decomposition of benzyl azides to give 1,3,5-triphenyl-2,4-diazapenta-1,4-diene (“hydrobenzamide”), benzyl-benzylideneamine, and benzonitrile. Reactions with the catalyst precursor [Cp∧RuCl2]2 are particularly fast and give hydrobenzamide with high selectivity. A similar coupling reaction is observed for other benzylic azides but not for (2-azidoethyl)benzene and ethyl-4-azidobutanoate. If the reactions are performed in the presence of water, benzylic azides are converted into aldehydes. Mononuclear tetrazene complexes are formed in stoichiometric reactions of [Cp∧RuCl2]2 with benzyl azide and (2-azidoethyl)benzene. |
| Databáze: | OpenAIRE |
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