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Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode
Author(s) -
Lombardi Lorenzo,
Bellini Daniele,
Bottoni Andrea,
Calvaresi Matteo,
Monari Magda,
Kovtun Alessandro,
Palermo Vincenzo,
Melucci Manuela,
Bandini Marco
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001373
Subject(s) - graphene , oxide , covalent bond , allylic rearrangement , catalysis , substrate (aquarium) , yield (engineering) , stereoselectivity , chemistry , grafting , combinatorial chemistry , stoichiometry , organic chemistry , nanotechnology , materials science , oceanography , polymer , geology , metallurgy
The site‐selective allylative and allenylative dearomatization of indoles with alcohols was 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 (H 2 O/CH 3 CN, 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 through simple acidic treatment was also documented.