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

chemistry

Author

Vincenzo Palermo

Chalmers, Industrial and Materials Science, Materials and manufacture

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Graphene Core Project 2 (Graphene Flagship)

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

Areas of Advance

Nanoscience and Nanotechnology (2010-2017)

Energy

Materials Science

Subject Categories

Materials Chemistry

Organic Chemistry

Infrastructure

Chalmers Materials Analysis Laboratory

DOI

10.1002/chem.202001373

More information

Created

6/3/2020 1