The reaction of aldehydes with N-methylpyrrole carried out in the presence of catalytic pyrrolidinium tetrafluoroborate at room temperature affords the corresponding dipyrromethanes and minor amounts of tripyrranes. This new, mild, and convenient process represents the first organocatalytic synthesis of dipyrromethanes. The products are obtained in chemical yields similar to those obtained with existing methods, which, however, require either a much larger excess of heterocycle (when aldehydes are employed as starting materials), or more drastic reaction conditions (when aldehyde equivalents are used as starting materials) than those employed here. A mechanism is proposed to explain the course of this reaction. (c) 2006 Elsevier Ltd. All rights reserved.

Organocatalytic synthesis of dipyrromethanes by the addition of N-methylpyrrole to aldehydes / C. Biaggi, M. Benaglia, L. Raimondi, F. Cozzi. - In: TETRAHEDRON. - ISSN 0040-4020. - 62:52(2006), pp. 12375-12379. [10.1016/j.tet.2006.09.104]

Organocatalytic synthesis of dipyrromethanes by the addition of N-methylpyrrole to aldehydes

C. Biaggi;M. Benaglia;L. Raimondi;F. Cozzi
2006

Abstract

The reaction of aldehydes with N-methylpyrrole carried out in the presence of catalytic pyrrolidinium tetrafluoroborate at room temperature affords the corresponding dipyrromethanes and minor amounts of tripyrranes. This new, mild, and convenient process represents the first organocatalytic synthesis of dipyrromethanes. The products are obtained in chemical yields similar to those obtained with existing methods, which, however, require either a much larger excess of heterocycle (when aldehydes are employed as starting materials), or more drastic reaction conditions (when aldehyde equivalents are used as starting materials) than those employed here. A mechanism is proposed to explain the course of this reaction. (c) 2006 Elsevier Ltd. All rights reserved.
catalysis ; organocatalysis ; heterocycles ; dipyrromethanes ; nucleophilic addition
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/24107
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 19
  • ???jsp.display-item.citation.isi??? 17
social impact