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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 53, 2023 - Issue 19
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Articles

Organocatalyzed Mannich reaction: Electrochemically synthesized prolinated carbon dots vs. prolinated graphene oxide

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Pages 1647-1663 | Received 08 Jun 2023, Published online: 02 Aug 2023
 

Abstract

Background

L-Pro was previously used as an organocatalyst in the Mannich reaction under homogeneous conditions; a recoverable catalyst could be useful; this is the first report on the application of prolinated carbon dots to the Mannich reaction.

Methods

Prolinated carbon dots were synthesized electrochemically using a bottom-up approach; they were characterized and used in the Mannich reaction in water using only a slight excess of ketone; for a useful comparison, L-proline decorated graphene oxide was synthesized.

Results

The characterization of carbon dots and functionalized graphene oxide confirmed the presence of L-Pro on their surface; their use in the Mannich reaction gave good yields when carrying out the reaction in water; a possible recycle of the catalyst was demonstrated.

Conclusions

Both electrochemically synthesized prolinated carbon dots and prolinated graphene oxide acted as organocatalysts in the Mannich reaction. Higher yields were obtained using L-Pro-CDs obtained under galvanostatic conditions.

GRAPHICAL ABSTRACT

Acknowledgment

The authors thank Marco Di Pilato for his help with the electrochemical experiments and CNIS technicians for nanoparticles characterization.

Author contributions

Conceptualization, M.F., M.B., and F.V.; methodology, M.B. and F.V.; investigation, M.B., D.R., and B.S.; resources, M.F., F.V.; data curation, D.R.; writing—original draft preparation, F.V. and M.B.; writing—review and editing, F.V.; visualization, F.V. and D.R.; supervision, M.F.; project administration, F.V. and M.F.; funding acquisition, M.F., F.V. All authors have read and agreed to the published version of the manuscript.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This research was funded by Sapienza University of Rome, [grant numbers RM12117A339284EE and RM1221814C52ED98].

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