Hydroaminomethylation of eugenol with Di-n-Butylamine (cas 111-92-2) catalyzed by rhodium complexes: Bringing light on the promoting effect of Brönsted acids
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Add time:08/21/2019 Source:sciencedirect.com
The hydroaminomethylation of eugenol with Di-n-Butylamine (cas 111-92-2) was performed employing a bis[(1,5-ciclooctadiene)(μ-methoxy)rhodium(I)] as pre-catalyst. In the absence of phosphines, the catalyst was efficient in the process, but the regioselectivity for amines was poor. For phosphine-promoted catalyst, the chemoselectivity at the hydroformylation step improved, but the hydrogenation of enamine intermediates was hampered. The regioselectivity within the class of amines was surprisingly high (>96%) for the linear product. The addition of triflic acid (10–20 mol%) improved significantly the efficiency of HAM. Employing the 2,2′-bis((diphenylphosphino)methyl)-1,1′-binaphthyl as ancillary and triflic acid as a promoter, the linear product was obtained in up to 93% yield.
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