Abstract
This work reports a highly regioselective hydroaminomethylation of eugenol, anethole and estragole with piperidine in aqueous medium. This catalytic system was composed of rhodium complexes stabilized by trisulfonated triphenylphosphine (TPPTS) and of a native or chemically modified cyclodextrins. Various cyclodextrins such as α-cyclodextrins (α-CD), β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), 2-hydroxy-propyl β-cyclodextrin (hp-β-CD) and RAndomly MEthylated β-cyclodextrin (RAME-β-CD) have been tested. The effect of different parameters such as syngas pressure, time, temperature, catalyst precursor/loading and the ratio of Metal/Ligand/Cyclodextrin were also investigated. The addition of cyclodextrins as a mass transfer agent remarkably increased the rate reaction and the selectivity of linear amines, specially in the case of RAME-β-CD. So, the Rh/TPPTS/RAME-β-CD as a catalyst exhibited high conversion (92%) and selectivity (79.2%) towards the linear amine as major product under mild conditions. Finally, the catalytic system was recycled up to five times without a significant loss in activity and selectivity.
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