Affiliation:
1. Department of Chemistry and Biochemistry Queens College of the City University of New York 65-30 Kissena Blvd. Queens New York 11367 United States
2. Ph.D. Program in Chemistry The Graduate Center of the City University of New York 365 Fifth Ave. New York New York 10016 United States
Abstract
Abstractn‐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.
Funder
Queens College, City University of New York
City University of New York