A new convenient synthesis of 5-aryl uracils using SRN1 aromatic nucleophilic substitution

✍ Scribed by Maurice Médebielle; Mehmet Ali Oturan; Jean Pinson; Jean-Michel Savéant

• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 266 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79168-4

✦ Synopsis

Direct and indirect electrochemical reduction of aryl halides in the presence of the uracil anion in dimethylsulfoxide yields the corrsponding S-aryl uracils by an SRNI mechanism.

Nucleophilic aromatic substitution catalyzed by electron injection (electrochemical, photochemical, solvated electrons, redox reagents). i.e.. reactions occurring by an SRNI mechanisml, have been shown to occur with a large variety of nucleophiles and leaving groups 2. Recently we have shown that pyrimidine anions could be good nucleophiles in the context of an SRNl mechanism with perfluoroalkyl iodides as subsuated.