Chemoselective Hydrogenation of α, β‐Unsaturated Carbonyls Catalyzed by Biomass‐Derived Cobalt Nanoparticles in Water. Issue 4 (18th January 2019)

• Record Type: Journal Article
• Authors: Song, Tao; Ma, Zhiming; Yang, Yong
• Is Part Of: ChemCatChem. Volume 11:Issue 4(2019)
• Page Start: 1313
• Page End: 1319
• Publication Date: 2019-01-18
• Subjects: nanostructured cobalt catalyst -- selective hydrogenation -- unsaturated ketones -- ketones -- one-pot method; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201801987
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: Herein, we report highly chemoselective hydrogenation of α, β‐unsaturated carbonyls to saturated carbonyls catalyzed by cobalt nanoparticles supported on the biomass‐derived carbon from bamboo shoots with molecular hydrogen in water, which is the first prototype using a heterogeneous non‐noble metal catalyst for such organic transformation as far as we know. The optimal cobalt nanocatalyst, CoOx @NC‐800, manifested remarkable activity and selectivity for hydrogenation of C=C in α, β‐unsaturated carbonyls under mild conditions. A broad set of α, β‐aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one‐pot cascade synthesis of saturated carbonyls was realized with high activity and selectivity via the cross‐aldol condensation of ketones with aldehydes followed by selective hydrogenation. More importantly, this one‐pot strategy is applicable for the expedient synthesis of Loureirin A, a versatile bioactive and medicinal molecule, from readily available starting materials, further highlighting the practical utility of the catalyst. In addition, the catalyst can be easily separated for successive reuses without significant loss in both activity and selectivity. Abstract : A heterogeneous and reusable biomass‐derived non‐noble cobalt nanoparticles has been firstly developed for efficient and selective hydrogenation of α, β‐unsaturated carbonyls to saturated carbonyls, and the direct one‐pot synthesis of saturated ketones including important bioactive and medical Loureirin A starting from aldehydes and ketones have also been realized in a sequential, cost‐effective, and green manner.