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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
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Selective amidation by a photocatalyzed umpolung reaction
Debasish Ghosh1, Rajesh Nandi1, Saikat Khamarui2
1Department of Chemistry, University of Calcutta, 92 A. P. C. Road, Kolkata-700009, India. dkmchem@caluniv.ac.in.
Chemical Communications (Cambridge, England)
|March 15, 2019
Summary
A novel metal-catalyzed reaction using eosin Y photocatalysis enables efficient synthesis of alpha-ketoamides under mild conditions. This method offers a scalable approach for producing diverse alpha-ketoamides and related compounds.
Area of Science:
- Organic Chemistry
- Photocatalysis
- Synthetic Methodology
Background:
- Metal-catalyzed reactions are crucial for organic synthesis.
- Photocatalysis offers mild and sustainable reaction conditions.
- Efficient synthesis of alpha-ketoamides remains a challenge.
Purpose of the Study:
- To develop a novel method for alpha-ketoamide synthesis.
- To combine metal catalysis with organophotocatalysis.
- To achieve synthesis under mild and scalable conditions.
Main Methods:
- Copper(I) iodide (CuI)-catalyzed COCH2-amidation.
- Synchronization with eosin Y (EY) organophotocatalyst.
- Reaction of 1,3-dicarbonyls with amines and PhIO under LED light.
Main Results:
- High selectivity and rapid production of alpha-ketoamides.
- Synthesis of diverse labile alpha-ketoamides, unsymmetrical oxalamides, and chiral analogues.
- Successful reaction under ambient temperature and mild conditions.
Conclusions:
- The developed strategy provides a new route for alpha-ketoamide synthesis.
- This approach integrates metal catalysis and photocatalysis effectively.
- The method is suitable for large-scale production in academic and industrial settings.
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