| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 41271 | Applied Catalysis A: General | 2012 | 7 Pages |
The hydroaminomethylation (hydroformylation/reductive amination) of the naturally occurring monoterpenes, i.e., limonene, camphene, and β-pinene, was studied having as condensation counterparts the amines di-n-butylamine, morpholine or n-butylamine. Moderate to good yields (75–94%) were obtained employing [Rh(cod)(μ-OMe)]2 as pre-catalyst in the presence or not of triphenylphosphine or tribenzylphosphine as ancillaries in toluene, at 100 °C and 60 bar of an equimolar mixture of carbon monoxide and hydrogen. Some of the hydroaminomethylation products derived from limonene have biological activity and the products derived from camphene and β-pinene are new.
Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (109 K)Download as PowerPoint slideHighlights► Naturally occurring monoterpenes were transformed into homologous amines. ► The transformation was made in one-pot (hydroaminomethylation). ► Rhodium complexes promote both hydroformylation and enamine hydrogenation. ► The concurrent double-bond isomerization was minimized by the use of phosphines. ► This study allowed insights about the nature of the catalytically active species.
