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Metal-free Photocatalytic Cross-Electrophile Coupling enables C1 Homologation and Alkylation of Carboxylic Acids with Aldehydes

Articolo
Data di Pubblicazione:
2024
Abstract:
In contemporary drug discovery, enhancing the sp3-hybridized character of molecular structures is paramount, necessitating innovative synthetic methods. Herein, we introduce a deoxygenative cross-electrophile coupling technique that pairs easily accessible carboxylic acid-derived redox-active esters with aldehyde sulfonyl hydrazones, employing Eosin Y as an organophotocatalyst under visible light irradiation. This approach serves as a versatile,metalfree C(sp3)−C(sp3) cross-coupling platform.We demonstrate its synthetic value as a safer, broadly applicable C1 homologation of carboxylic acids, offering an alternative to the traditional Arndt-Eistert reaction. Additionally, our method provides direct access to cyclic and acyclic β-arylethylamines using diverse aldehyde-derived sulfonyl hydrazones.Notably, the methodology proves to be compatible with the late-stage functionalization of peptides on solid-phase, streamlining the modification of intricate peptides without the need for exhaustive de-novo synthesis.
Tipologia CRIS:
1.1 Articolo in rivista
Keywords:
photocatalysis, dyes, eosin, C1 Homologation , Aldehydes
Elenco autori:
Bonciolini, S.; Pulcinella, A.; Leone, M.; Schiroli, D.; Luguera Ruiz, A.; Sorato, A.; Dubois, M.; Gopalakrishnan, R.; Masson, G.; Della Ca’, N.; Protti, S.; Fagnoni, M.; Zysman-Colman, E.; Johansson, M.; Noël, T.
Autori di Ateneo:
FAGNONI MAURIZIO
PROTTI STEFANO
Link alla scheda completa:
https://iris.unipv.it/handle/11571/1491536
Pubblicato in:
NATURE COMMUNICATIONS
Journal
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URL

https://www.nature.com/articles/s41467-024-45804-z
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