Using thioureas as H-bonding organocatalysts, nitroalkenes can be activated for the conjugate addition of hydrazones as neutral nucleophiles. Formaldehyde derivatives react at the azomethine carbon as expected, whereas hydrazones from enolizable aldehydes behave as ene-hydrazines and react at the alpha-carbon instead. Ionic liquids were found to decrease the reaction times considerably compared to commonly used solvents, whereas alter- native activation by Lewis acids resulted in decomposition of reactants.

A Broadened Scope for the Use of Hydrazones as Neutral Nucleophiles Using H-Bonding Organocatalysts / Pettersen, Daniel; Herrera, Raquel P.; Bernardi, Luca; Fini, Francesco; Sgarzani, Valentina; Fernandez, Rosario; Lassaletta, José M.; Ricci, Alfredo. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 2006:2(2006), pp. 239-242. [10.1055/s-2005-922791]

A Broadened Scope for the Use of Hydrazones as Neutral Nucleophiles Using H-Bonding Organocatalysts

FINI, Francesco;
2006

Abstract

Using thioureas as H-bonding organocatalysts, nitroalkenes can be activated for the conjugate addition of hydrazones as neutral nucleophiles. Formaldehyde derivatives react at the azomethine carbon as expected, whereas hydrazones from enolizable aldehydes behave as ene-hydrazines and react at the alpha-carbon instead. Ionic liquids were found to decrease the reaction times considerably compared to commonly used solvents, whereas alter- native activation by Lewis acids resulted in decomposition of reactants.
2006
23-dic-2005
2006
2
239
242
A Broadened Scope for the Use of Hydrazones as Neutral Nucleophiles Using H-Bonding Organocatalysts / Pettersen, Daniel; Herrera, Raquel P.; Bernardi, Luca; Fini, Francesco; Sgarzani, Valentina; Fernandez, Rosario; Lassaletta, José M.; Ricci, Alfredo. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 2006:2(2006), pp. 239-242. [10.1055/s-2005-922791]
Pettersen, Daniel; Herrera, Raquel P.; Bernardi, Luca; Fini, Francesco; Sgarzani, Valentina; Fernandez, Rosario; Lassaletta, José M.; Ricci, Alfredo
File in questo prodotto:
File Dimensione Formato  
05 - Synlett 2006 Pettersen 239-242.pdf

Accesso riservato

Descrizione: Articolo Principale
Tipologia: Versione pubblicata dall'editore
Dimensione 58.5 kB
Formato Adobe PDF
58.5 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Licenza Creative Commons
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1122086
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 26
  • ???jsp.display-item.citation.isi??? 25
social impact