Nitrogen-Rich Carbon Dots as Effective Catalysts in the 1,4-Reduction of α,β-Unsaturated Aldehydes via Ion Pair Asymmetric Nano-Organocatalysis
The development of nanostructured organocatalysts is emerging as a prominent field in materials science. To this purpose, nitrogen-doped carbon dots (CDs) have been effectively employed in enantioselective enamine organocatalysis. On the other hand, enantioselective iminium ion nano-organocatalysis is much less explored. In this Letter, the use of CDs in asymmetric iminium ion catalysis via asymmetric counteranion-directed catalysis (ACDC) is disclosed. Nonchiral CDs bearing butylenediamine residues proved to be the most effective ones, in combination with (S)-TRIP as a chiral phosphoric acid (CPA). A correlation between the features of the CDs’ surfaces and their catalytic performance was shown, and the catalytic activity of the employed CDs proved to be higher than that of simple molecular amines. An extensive reaction optimization allowed the reduction of different α,β-unsatured aldehydes in good yield and ee, using a low catalyst loading.
Authors
- Fabio Pesciaioli (ORCID: https://orcid.org/0000-0002-6792-6292)
- Martina Mamone (ORCID: https://orcid.org/0000-0001-5981-1295)
- Giuseppe Gentile (ORCID: https://orcid.org/0000-0002-5622-8579)
- Armando Carlone (ORCID: https://orcid.org/0000-0003-2983-6445)
- Maurizio Prato (ORCID: https://orcid.org/0000-0002-8869-8612)
- Giuliana Giorgianni
- Maria Edith Casacchia (ORCID: https://orcid.org/0000-0002-3435-2923)
- Giacomo Filippini (ORCID: https://orcid.org/0000-0002-9694-3163)
- Emanuele Cocco (ORCID: https://orcid.org/0000-0002-6176-0535)
- Alessio Carioscia (ORCID: https://orcid.org/0000-0002-2091-1173)
- Elena Incerto
Institutions
- Ikerbasque (ES)
- University of Trieste (IT)
- University of L'Aquila (IT)
- Istituto Universitario di Studi Superiori di Pavia (IT)
- CIC biomaGUNE (ES)
- National Interuniversity Consortium of Materials Science and Technology (IT)
Publication Details
- Journal
- ACS Catalysis
- Published
- 2024-08-23
- DOI
- https://doi.org/10.1021/acscatal.4c03532
- Citations
- 12
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- Consorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali
- Ministero dell’Istruzione, dell’Università e della Ricerca
- Università degli Studi dell'Aquila
- Regione Autonoma Friuli Venezia Giulia
- Università degli Studi di Trieste
- Ministero dell'Università e della Ricerca
- European Research Council