Allylic and Allenylic Dearomatization of Indoles promoted by Graphene Oxide via Covalent Grafting Activation Mode
Journal article, 2020
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.
nanocarbon
dehydrogeneation
chemistry
ethylbenzene
graphene
Author
Daniele Bellini
University of Bologna
Andrea Bottoni
University of Bologna
Matteo Calvaresi
University of Bologna
Magda Monari
University of Bologna
Alessandro Kovtun
Institute for organic syntheses and photoreactivity (ISOF-CNR)
Vincenzo Palermo
Institute for organic syntheses and photoreactivity (ISOF-CNR)
Chalmers, Industrial and Materials Science, Materials and manufacture
Manuela Melucci
Institute for organic syntheses and photoreactivity (ISOF-CNR)
Marco Bandini
Consorzio C.I.N.M.P.I.S.
University of Bologna
Chemistry - A European Journal
0947-6539 (ISSN) 1521-3765 (eISSN)
Vol. 26 46 10427-10432Graphene Core Project 2 (Graphene Flagship)
European Commission (EC) (EC/H2020/785219), 2018-04-01 -- 2020-03-31.
Areas of Advance
Nanoscience and Nanotechnology
Energy
Materials Science
Subject Categories
Materials Chemistry
Organic Chemistry
Infrastructure
Chalmers Materials Analysis Laboratory
DOI
10.1002/chem.202001373