One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)

In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, alde...

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Bibliographic Details
Published inCatalysis communications Vol. 9; no. 6; pp. 1066 - 1070
Main Authors Graebin, Cedric S., Eifler-Lima, Vera Lucia, da Rosa, Ricardo G.
Format Journal Article
LanguageEnglish
Published AMSTERDAM Elsevier B.V 31.03.2008
Elsevier
Subjects
Chemistry
Chemistry, Physical
Hydroaminomethylation
Hydroformylation
Limonene
Physical Sciences
Science & Technology
Secondary amines
Terpenes
Tertiary amines
Limonene
Tertiary amines
Hydroaminomethylation
Terpenes
Secondary amines
Hydroformylation
limonene
tertiary amines
DIENES
hydroaminomethylation
terpenes
RHODIUM-CATALYZED HYDROFORMYLATION
secondary amines
METAL
hydroformylation
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Summary:In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, aldehyde/amine condensation and imine/enamine hydrogenation. Hydroaminomethylation, besides the high yields, has a high atom economy because just 1 mol of water is wasted per mol of limonene. Due to our catalytic optimizations, the reaction time was reduced from 48 h (described in the literature) to 10–24 h, as well as limonene isomerization was strongly minimized by the triphenylphosphine added.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2007.10.008