Ruthenium-Catalyzed Sequential Enyne Cross-Metathesis/ATRA Reactions

✍ Scribed by Gregor Kiefer; Jesus Ruiz; Euro Solari; Gerhard Hilt; Kay Severin

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 309 KB
• Volume: 2012
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101263

✦ Synopsis

Abstract

Sequential enyne cross‐metathesis reactions of arylalkynes with ethylene followed by atom transfer radical addition (ATRA) with ethyl dichloroacetate or dichloroacetonitrile provide 1,5‐dichloropent‐2‐ene derivatives. The second‐generation Grubbs alkylidene complex [RuCl~2~(=CHPh)(PCy~3~)(NHC)] [NHC = 1,3‐bis(2,4,6‐trimethylphenyl)‐2‐imidazolidinylidene] is used as the catalyst precursor for both reactions. Preliminary results show that the reaction products can be converted into vinylcyclopropanes by dechlorination with magnesium or manganese.