Applied Catalysis A: General, Vol.411, 70-76, 2012
An efficient method for the transformation of naturally occurring monoterpenes into amines through rhodium-catalyzed hydroaminomethylation
The hydroaminomethylation (hydroformylation/reductive amination) of the naturally occurring monoterpenes, i.e., limonene, camphene, and beta-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)(mu-OMe)](2) as pre-catalyst in the presence or not of triphenylphosphine or tribenzylphosphine as ancillaries in toluene, at 100 degrees 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 beta-pinene are new. (C) 2011 Elsevier BM. All rights reserved.