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Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcohols via C–H bond activation

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Abstract

The first Fe-catalysed alkylation of 2-methyl and 4-methyl-azaarenes with a series of alkyl and hetero-aryl alcohols is reported (>39 examples and up to 95% yield). Multi-functionalisation of pyrazines and synthesis of anti-malarial drug (±) Angustureine significantly broaden the scope of this methodology. Preliminary mechanistic investigation, deuterium labeling and kinetic experiments including trapping of the enamine intermediate 1a′ are of special importance.

Graphical abstract: Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcohols via C–H bond activation

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Article information


Submitted
29 Feb 2020
Accepted
10 Mar 2020
First published
10 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Iron-catalysed alkylation of 2-methyl and 4-methyl azaarenes with alcohols via C–H bond activation

L. M. Kabadwal, S. Bera and D. Banerjee, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01593H

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