Gold Catalysis for Selective Hydrogenation of Aldehydes and Valorization of Bio-Based Chemical Building Blocks

Author(s)

Silva, Rerison J. M. ^[1] ; Fiorio, Jhonatan L. ^[1] ; Vidinha, Pedro ^[1] ; Rossi, Liane M. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 30, n. 10, SI, p. 2162-2169, OCT 2019.
• Web of Science Citations: 0

Abstract

Gold catalysts are best known for their selectivity in oxidation reactions, however, there is a promising future for gold in selective hydrogenations. Herein, the hydrogenation of several aldehydes and important bio-based chemical building blocks, namely 5-hydroxymethylfurfural (5-HMF), furfural and vanillin, was performed throughout the combination of Au nanoparticles with Lewis bases. The Au-amine ligand (e.g.. 2,4,6-trimethylpyridine) catalytic system could reduce the aldehyde carbonyl group selectively, without reducing alkene moieties or opening the furanic ring that occur on most traditional catalysts. Otherwise, the reduction of nitro group is preferential and the catalytic system was used for the synthesis of furfurylamines, important intermediates in the synthesis of different pharmaceuticals (e.g., furosemide), through the selective reductive amination of furfural starting from nitro-compounds. Moreover, a fully heterogeneous gold catalyst embedded in N-doped carbon (Au@N-doped carbon/TiO2) was able to perform these reactions in successive recycles without the addition of ligands, with impact in the development of a continuous flow process for biomass valorization. (AU)

• FAPESP's process: 16/16738-7 - Study of the influence of organic ligands on the reactivity of gold nanoparticles
• Grantee: Liane Marcia Rossi
• Support Opportunities: Regular Research Grants