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.
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