Hydrogenation of α,β-Unsaturated Carbonyl Compounds Using Recyclable Water-Soluble FeII/EDTA Complex Catalyst

Abstract

Hydrogenation of unsaturated carbonyl compounds like cinnamaldehyde and citral was studied in a biphasic media using water-soluble Fe II /EDTA as a catalyst. It was observed that olefinic bond was selectively hydrogenated over the carbonyl group. Different reaction parameters like temperature, pressure, catalyst concentration were optimized for better selectivity of hydrocinnamaldehyde/ dihydrocitronellal. The catalyst was further extended to hydrogenation of several other a,b-unsaturated carbonyl compounds.

Homogeneous catalysis using iron complexes: recent developments in selective reductions

“…More recently, Bhanage and co-workers hydrogenated selectively the CQC double bond of a,b-unsaturated carbonyl compounds in a biphasic medium using water-soluble Fe II /Na 2 EDTA as a catalyst which can be easily recycled (Scheme 4). 10 Using citral as a model substrate a catalyst system consisting of FeSO 4 Á7H 2 O and Na 2 EDTAÁ2H 2 O showed the best activity and selectivity towards saturated dihydrocitronellal (82%). Other a,b-unsaturated carbonyl compounds were hydrogenated with the Fe II /Na 2 EDTA catalyst at 100 1C.…”

Biphasic Hydrogenation of α,β-unsaturated Aldehydes with Hydrosoluble Rhodium and Ruthenium Complexes

“…1), have found many uses in the fragrance, cosmetics, flavor, and pharmacological industries; also, they constitute relevant intermediates in the synthesis of various fine chemicals [1,2]. The reaction is complicated by the presence of two moieties with similar reactivity: the carbonyl group and the olefin carbon-carbon double bond; in practice, it's desired that only one of them reacts, and this has been a very prolific research field over the years.…”

Highly efficient and chemoselective hydrogenation of α,β-unsaturated carbonyls over Pd/N-doped hierarchically porous carbon

“…Chemoselective hydrogenation of α,β-unsaturated carbonyls is fundamentally important as it has extensive applications in the synthesis of fine chemicals, pharmaceuticals and functional materials. [1][2][3][4] The selectivity varies due to the possibility of hydrogenation of either the CC bond or the CO bond, or both of them (Scheme 1). The selective hydrogenation of the CC bond is an important industrial process in which heterogeneous catalysts, especially supported precious metal catalysts, have attracted much attention due to the ease of their separation and recycling together with their outstanding performances.…”