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

Sandra M. Rountree, Rebecca Taylor, Christopher Hardacre, M. Cristina Lagunas, Paul N. Davey

    Research output: Contribution to journalArticlepeer-review

    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
    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

    Fingerprint

    Dive into the research topics of 'Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs’ catalysts'. Together they form a unique fingerprint.

    Cite this