Eucalyptol: An Alternative Green Solvent for the Michael Addition of Indoles to α, β‐Unsaturated Ketones and Nitrostyrenes

Reduction of carbon footprint generated by organic solvents via replacing them with greener solvents is of great interest in recent times. Herein, we report a Michael addition reaction of indoles to α, β‐unsaturated ketones, and nitrostyrene using reusable and low toxic eucalyptol as a green solvent...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2022-07, Vol.7 (25), p.n/a
Main Authors: Dave, Alpa Y., Mishra, Akanksha, Talukdar, Mrinal, Begari, Eeshwaraiah
Format: Article
Language:English
Subjects:
Bio-based solvent Eucalyptol
Indoles
Michael addition
α, β-Unsaturated Ketones
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Summary:Reduction of carbon footprint generated by organic solvents via replacing them with greener solvents is of great interest in recent times. Herein, we report a Michael addition reaction of indoles to α, β‐unsaturated ketones, and nitrostyrene using reusable and low toxic eucalyptol as a green solvent, and Fe(OTs)3 ⋅ 6H2O as green catalyst. This methodology offers broad substrate scope and excellent yields (up to 90 %) in short reaction times. Herein, we report protocol for the synthesis of 3‐alkylated indole derivatives using eucalyptol as an eco‐friendly, reusable, and sustainable bio‐solvent along with Fe(OTs)3 ⋅ 6H2O as green catalyst for the first time. Diverse chalcones and b‐nitrostyrenes underwent Michael addition reaction with indoles to give corresponding 3‐substituted indole derivatives. This method offers excellent substrate scope (24 examples) and yields (up to 90 %) in short reaction times and recyclable, low‐toxic eucalyptol as a green alternative bio‐solvent to replace the traditional fossil fuel‐based solvents.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202200954