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Issue 9, 2011
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Rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins

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Abstract

A rhodium-grafted hydrotalcite (Rh/HT) was prepared by the treatment of a Mg–Al mixed hydroxide (hydrotalcite, HT) with an aqueous RhCl3·nH2O solution. The formation of the RhIII species on the HT surface was confirmed by X-ray absorption fine structure spectroscopy. The Rh/HT catalyst was demonstrated to effectively promote the 1,4-addition reaction of organoboron reagents to electron-deficient olefins in both organic and aqueous solvents. The strong surface basicity of HT facilitates the formation of a Rh–OH species, which possesses high nucleophilicity, leading to an efficient transmetalation with organoboron reagents. This catalyst system is also applicable in the one-pot three-component synthesis of 2-cyano-3,3-diphenyl propionate due to the bifunctionality of the Rh/HT surface.

Graphical abstract: Rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins

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Publication details

The article was received on 08 Feb 2011, accepted on 09 May 2011 and first published on 12 Jul 2011


Article type: Paper
DOI: 10.1039/C1GC15146K
Citation: Green Chem., 2011,13, 2416-2422
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    Rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins

    K. Motokura, N. Hashimoto, T. Hara, T. Mitsudome, T. Mizugaki, K. Jitsukawa and K. Kaneda, Green Chem., 2011, 13, 2416
    DOI: 10.1039/C1GC15146K

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