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.

graphene

ethylbenzene

nanocarbon

dehydrogeneation

chemistry

Author

Daniele Bellini

University of Bologna

Andrea Bottoni

University of Bologna

Matteo Calvaresi

University of Bologna

Magda Monari

University of Bologna

Alessandro Kovtun

Istituto per la Sintesi Organica e la Fotoreattività

Vincenzo Palermo

Istituto per la Sintesi Organica e la Fotoreattività

Chalmers, Industrial and Materials Science, Materials and manufacture

Manuela Melucci

Istituto per la Sintesi Organica e la Fotoreattività

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 10427-10432

Graphene Core Project 2 (Graphene Flagship)

European Commission (EC), 2018-04-01 -- 2020-03-31.

Areas of Advance

Nanoscience and Nanotechnology (SO 2010-2017, EI 2018-)

Energy

Materials Science

Subject Categories

Materials Chemistry

Organic Chemistry

Infrastructure

Chalmers Materials Analysis Laboratory

DOI

10.1002/chem.202001373

More information

Latest update

9/10/2020