Synthesis of , of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs’ catalysts

Sandra M. Rountree, Sarah F.R. Taylor, Christopher Hardacre, M. Cristina Lagunas*, Paul N. Davey

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A series of alpha,beta-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs' catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest, as it has not previously being used as a substrate in cross-metathesis reactions and allows access to valuable intermediates for the synthesis of new fragrances. Most reactions gave good selectivity of the desired CM product (>= 90%). Detailed optimisation and mechanistic studies have been performed on the cross-metathesis of acrolein with 1-decene. Recycling of the catalyst has been attempted using ionic liquids. 

Original languageEnglish
Pages (from-to)94-104
Number of pages11
JournalApplied Catalysis A: General
Volume486
Early online date02 Sep 2014
DOIs
Publication statusPublished - 22 Sep 2014

Keywords

  • Cross-metathesis
  • Grubbs' catalysts
  • Acrolein
  • Fragrances
  • FATTY-ACID DERIVATIVES
  • HETEROCYCLIC CARBENE LIGANDS
  • SELECTIVE OLEFIN METATHESIS
  • TEMPERATURE IONIC LIQUIDS
  • QUATERNARY AMMONIUM GROUP
  • RING-CLOSING METATHESIS
  • DIELS-ALDER REACTIONS
  • METHYL ACRYLATE
  • UNSATURATED ALDEHYDES
  • RUTHENIUM CATALYSTS

ASJC Scopus subject areas

  • Chemistry(all)

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