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- Title
n‐Bu<sub>4</sub>NI/K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>‐Mediated C−N Coupling Between Aldehydes and Amides.
- Authors
Liu, Xiaochen; Hee, Samual; Sapir, Netanel G.; Li, Alvin; Farkruzzaman, Syed; Liu, Jianbo; Chen, Yu
- Abstract
n‐Bu4NI/K2S2O8 mediated C−N coupling between aldehydes and amides is reported. A strong electronic effect is observed on the aromatic aldehyde substrates. The transformylation from aldehyde to amide takes place exclusively when an aromatic aldehyde bears electron‐donating groups at either the ortho or para position of the formyl group, while the cross‐dehydrogenative coupling dominates in the absence of these groups. Both the density functional theory (DFT) thermochemistry calculations and experimental data support the proposed single electron transfer mechanism with the formation of an acyl radical intermediate in the cross‐dehydrogenative coupling. The n‐Bu4NI/K2S2O8 mediated oxidative cyclization between 2‐aminobenzamide and aldehydes is also reported, with four quinazolin‐4(3H)‐ones prepared in 65–99 % yields.
- Subjects
SINGLE electron transfer mechanisms; ALDEHYDES; AMIDES; AROMATIC aldehydes; POLAR effects (Chemistry); DENSITY functional theory
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 23, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400067