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.

Lorenzo Lombardi, D.B. (2020). Allylic and Allenylic Dearomatization of Indoles promoted by Graphene Oxide via Covalent Grafting Activation Mode. CHEMISTRY-A EUROPEAN JOURNAL, 26(46), 10427-10432 [10.1002/chem.202001373].

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, D.B. (2020). Allylic and Allenylic Dearomatization of Indoles promoted by Graphene Oxide via Covalent Grafting Activation Mode. CHEMISTRY-A EUROPEAN JOURNAL, 26(46), 10427-10432 [10.1002/chem.202001373].
Lorenzo Lombardi, Daniele Bellini, Andrea Bottoni, Matteo Calvaresi, Magda Monari, Alessandro Kovtun, Vincenzo Palermo, Manuela Melucci, Marco Bandini...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/771343
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