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An efficient method for the transformation of naturally occurring monoterpenes into amines through rhodium-catalyzed hydroaminomethylation

Paper ID Volume ID Publish Year Pages File Format Full-Text
41271 45883 2012 7 PDF Available
Title
An efficient method for the transformation of naturally occurring monoterpenes into amines through rhodium-catalyzed hydroaminomethylation
Abstract

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.

Keywords
Hydroaminomethylation; Hydroformylation; Amination; Monoterpene; Tandem catalysis
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An efficient method for the transformation of naturally occurring monoterpenes into amines through rhodium-catalyzed hydroaminomethylation
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 411–412, 16 January 2012, Pages 70–76
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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