One-step synthesis of ketones from biobased 5-hydroxymethylfurfural (5-HMF) and its derivatives is reported. Bipyridine coordinated Cp*-Iridium(III) complexes exhibit highly efficient catalytic performance for hydrogenation/hydrolytic ring opening of 5-HMF and derivatives to produce ketones. A bipyridine ligand with both dimethylamino and ortho-hydroxyl groups achieved a 1-hydroxyhexane-2,5-dione (HHD) formation turnover frequency (TOF) of 31 560 h−1 by H2 and a TOF of 6140 h−1 by formic acid. The catalytic mechanism is proposed to proceed via carbonyl hydrogenation, hydroxyl group promoted and directed hydrolytic furan ring opening, followed by hydrogenation of α,β-unsaturated carbonyl compound based on the experimental and independent events' statistical calculation results.<br/>References: ACS Catal. 2015, 5, 788; ACS Catal. 2016, 6, 3784.

Hydrogenation of biomass based furans to fine chemicals through homogeneous Ir catalysis

255th National Meeting (2018)

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