Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles
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Título: | Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles |
Autor/a: | Bernárdez Alfaya, Rodrigo Suárez Rivero, Jaime Fañanás Mastral, Martín Varela Carrete, Jesús Ángel Saá Rodríguez, Carlos |
Centro/Departamento: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Palabras chave: | Hydrocarbons | Reactions products | Catalysis | Isomerization | Brönsted-acid | Chain walking | Ruthenium | |
Data: | 2016 |
Editor: | American Chemical Society |
Cita bibliográfica: | Bernárdez, R., Suárez, J., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2016). Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxa-zaheterocycles. Org. Lett., 18, 4, 642-645 |
Resumo: | A novel route to 1,3-oxazaheterocycles based on cooperative Ru–H/Brønsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)3 complex allows for an efficient long distance chain-walking process while the Brønsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst. |
Descrición: | NOTICE: This is the peer reviewed version of the following article: Bernárdez, R., Suárez, J., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2016). Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles. Org. Lett., 18, 4, 642-645. [doi: 10.1021/acs.orglett.5b03499]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving. |
Versión do editor: | https://doi.org/10.1021/acs.orglett.5b03499 |
URI: | http://hdl.handle.net/10347/23351 |
DOI: | 10.1021/acs.orglett.5b03499 |
ISSN: | 1523-7060 |
E-ISSN: | 1523-7052 |
Dereitos: | Copyright © 2016 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving. |
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