Chemoselective Atmospheric Hydrogenation of Two C═C bonds of α,β-Unsaturated Diketones Derived from Biobased 5-Hydroxymethylfurfural Catalyzed by a Metal-Ligand Bifunctional Iridium Catalyst.

Chemoselective atmospheric hydrogenation of two C═C bonds of α,β-unsaturated diketones derived from 5-hydroxymethylfurfural (5-HMF) has been accomplished. In the presence of [Cp*Ir(2,2'-bpyO)(OH2)] (0.5 mol %), a series of desired products were obtained in high yields with excellent selectivity. It was found that functional groups in the bpy ligand are crucially important for the catalytic activity. Furthermore, DFT calculations, the application of this strategy for the construction of an aromatic compound, and chemoselective atmospheric hydrogenation of a C═C bond of α,β-unsaturated ketones derived from other biobased furfuryl aldehydes were also presented.