ETD

Archivio digitale delle tesi discusse presso l'Università di Pisa

Tesi etd-09282016-145651


Tipo di tesi
Tesi di laurea magistrale
Autore
PEZZETTA, CRISTOFER
URN
etd-09282016-145651
Titolo
The Murai Reaction on Furfural Derivatives
Dipartimento
CHIMICA E CHIMICA INDUSTRIALE
Corso di studi
CHIMICA
Relatori
relatore Prof. Bellina, Fabio
Parole chiave
  • organometallics
  • organometalli
  • Murai
  • idroarilazione
  • hydroarylation
  • furfurale
  • furfural
  • catalysis
  • catalisi
  • biomassa
  • biomass
  • rutenio
  • ruthenium
  • sintesi
  • synthesis
Data inizio appello
20/10/2016
Consultabilità
Completa
Riassunto
Furfural and related compounds are industrially relevant-building blocks obtained from renewable resources; growing attention arose in recent years towards their utilisation as precursors for bulk and fine chemicals, being a “green” alternative to petroleum-based compounds. Several works reported the functionalisation of furfurals to obtain a wider range of chemicals, opening to new possibilities for synthesis and applications. C-H activation-based processes are the most attracting, for their atom economy and the possibility to employ non-activated substrates. In the case of furfural derivatives, the main results are in the field of arylation reactions.
In this work, the directed hydroarylation of olefins (Murai reaction) on furfural derivatives has been investigated. A method for the formal insertion of olefins, especially vinylsilanes, into the C3-H bond of furfural has been developed. Different conditions and substrates have been tested, discovering that only a bidentate directing group is capable of providing good yields of the coupling products. As an added bonus, easy removal of the directing group is achieved during the work-up.
These results represent one of the few examples of alkylation of furfurals through C-H activation reactions, and the only one occurring at the C3 position of the furan ring.
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