Regioselective hydroaminomethylation of vinylarenes by a sol-gel immobilized rhodium catalyst

Zackaria Nairoukh, Jochanan Blum*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


In the course of our studies toward the development of new heterogeneous conditions for better controlling regioselectivity in organic reactions, we investigated the application of sol-gel immobilized organometallic catalyst for regioselective hydroaminomethylation of vinylarenes with aniline or nitroarene derivatives in an aqueous microemulsion. By immobilization of 6 mol % [Rh(cod)Cl]2 within a hydrophobic silica sol-gel matrix we were able to perform efficient hydroaminomethylation under mild conditions and isolate 2-arylpropylamines with high regioselectivity. The regioselectivity of the reaction was found to be mainly dependent on the hydrophobicity of the catalyst support. It is also significantly affected by the electronic nature of the substrates, by the reaction temperature, and by syngas pressure. The heterogenized catalyst can be reused for several times.

Original languageAmerican English
Pages (from-to)2397-2403
Number of pages7
JournalJournal of Organic Chemistry
Issue number6
StatePublished - 21 Mar 2014


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