The graphene oxide (GO) assisted allylic alkylation of thiophenes with alcohols is presented. Mild reaction conditions and a low GO loading enabled the isolation of a range of densely functionalized thienyl and bithienyl compounds in moderate to high yields (up to 90%). The cooperative action of the Bronsted acidity, epoxide moieties, and pi-surface of the 2D-promoter is highlighted as crucial in the reaction course of the present Friedel-Crafts-type protocol.

Graphene Oxide Promotes Site-Selective Allylic Alkylation of Thiophenes with Alcohols

AN, JUZENG
Membro del Collaboration Group
;
Assunta De Nisi
Membro del Collaboration Group
;
Manuela Melucci
Supervision
;
PALERMO, VINCENZO
Membro del Collaboration Group
;
Andrea Bottoni
Writing – Review & Editing
;
Francesco Zerbetto
Writing – Review & Editing
;
Matteo Calvaresi
Data Curation
;
Marco Bandini
Writing – Original Draft Preparation
2018

Abstract

The graphene oxide (GO) assisted allylic alkylation of thiophenes with alcohols is presented. Mild reaction conditions and a low GO loading enabled the isolation of a range of densely functionalized thienyl and bithienyl compounds in moderate to high yields (up to 90%). The cooperative action of the Bronsted acidity, epoxide moieties, and pi-surface of the 2D-promoter is highlighted as crucial in the reaction course of the present Friedel-Crafts-type protocol.
2018
Laura Favaretto, Juzeng An, Marco Sambo, Assunta De Nisi, Cristian Bettini, Manuela Melucci, Alessandro Kovtun, Andrea Liscio, Vincenzo Palermo, Andrea Bottoni, Francesco Zerbetto, Matteo Calvaresi, Marco Bandini
File in questo prodotto:
File Dimensione Formato  
ol8b01531_si_001.pdf

accesso aperto

Tipo: File Supplementare
Licenza: Licenza per accesso libero gratuito
Dimensione 1.53 MB
Formato Adobe PDF
1.53 MB Adobe PDF Visualizza/Apri
Graphene oxide promotes.. (OLETT-Bandini-revision-no-colors)-4.pdf

Open Access dal 05/06/2020

Tipo: Postprint
Licenza: Licenza per Accesso Aperto. Altra tipologia di licenza compatibile con Open Access
Dimensione 921.25 kB
Formato Adobe PDF
921.25 kB Adobe PDF Visualizza/Apri

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: https://hdl.handle.net/11585/639182
Citazioni
  • ???jsp.display-item.citation.pmc??? 2
  • Scopus 27
  • ???jsp.display-item.citation.isi??? 24
social impact