The site-selective allylative and allenylative dearomatization of indoles with alcohols is performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt% loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92%) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst via simple acidic treatment was also documented.

Allylic and Allenylic Dearomatization of Indoles promoted by Graphene Oxide via Covalent Grafting Activation Mode

Lorenzo Lombardi
Methodology
;
Andrea Bottoni
Methodology
;
Matteo Calvaresi
Conceptualization
;
Magda Monari
Methodology
;
Manuela Melucci
Methodology
;
2020

Abstract

The site-selective allylative and allenylative dearomatization of indoles with alcohols is performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt% loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92%) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst via simple acidic treatment was also documented.
2020
Lorenzo Lombardi, Daniele Bellini, Andrea Bottoni, Matteo Calvaresi, Magda Monari, Alessandro Kovtun, Vincenzo Palermo, Manuela Melucci, Marco Bandini
File in questo prodotto:
File Dimensione Formato  
Allylic and Allenylic (post-print).docx

Open Access dal 28/04/2021

Tipo: Postprint
Licenza: Creative commons
Dimensione 1.48 MB
Formato Microsoft Word XML
1.48 MB Microsoft Word XML Visualizza/Apri
Allylic and Allenylic......(total).pdf

accesso aperto

Tipo: File Supplementare
Licenza: Licenza per accesso libero gratuito
Dimensione 11.09 MB
Formato Adobe PDF
11.09 MB 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/11585/771343
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 14
  • ???jsp.display-item.citation.isi??? 14
social impact