An efficient chemoselective reduction of furan series unsaturated dinitriles

• Published in: Molecules (Basel, Switzerland) Vol. 18; no. 2; pp. 2212 - 2221
• Main Authors: Bobal, Pavel, Bobalova, Janette
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 11-02-2013; MDPI
• Subjects: 2-phenylbenzimidazoline; Atmospheric pressure; Chemistry; chemoselective reduction; conjugated olefins; Decomposition; furan ethylenes; Furans - chemical synthesis; Furans - chemistry; Hydrogenation; Nitriles - chemistry; organic hydride compounds; Oxidation-Reduction; regioselective reduction; unsaturated dinitriles; Czech Republic
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules18022212

An efficient reduction of double bonds conjugated with nitrile groups and acid or base sensitive furan rings with 2-phenylbenzimidazoline generated in situ has been successfully accomplished with high yields and excellent selectivity. The employed reducing agent was prepared in one step from ordinary chemicals. The other advantages of the presented method include mild and convenient reaction conditions, a benign and cost effective reagent, simple work-up and separation of the products. As this process does neither affect cyano and nitro groups nor furan rings, it is a valuable alternative when metal-catalyzed hydrogenations or borohydride reductions have failed.