Formation and Reactivity of Bis-Anions derived from Furoic Acids

✍ Scribed by David W. Knight

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 203 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93535-x

✦ Synopsis

Ode of the most versatile methods for the homologation of furans is the coupling of simple metallated furans with electrophiles. The metallated species can be formed either by metalhalogen exchange"* (e.g. 3-furyllithium from a 3-halofuran and n-butyl lithium) or by the direct metallation of the furan nucleus, normally with n-butyl lithium. 3,4 In this note, we wish to report that furoic acids undergo efficient and regioselective ring metallation on reaction with lithium diisopropylamide (LDA) to give bis-anionic species which react well with a number of electrophiles.