Electrocatalytic synthesis of heterocycles from biomass-derived furfuryl alcohols

Xuan Liu, Bo Li, Guanqun Han, Xingwu Liu, Zhi Cao (), Jiang De-en () and Yujie Sun ()
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Xuan Liu: University of Cincinnati
Bo Li: University of California
Guanqun Han: University of Cincinnati
Xingwu Liu: Syncat@Beijing, Synfuels CHINA Co., Ltd
Zhi Cao: Syncat@Beijing, Synfuels CHINA Co., Ltd
Jiang De-en: University of California
Yujie Sun: University of Cincinnati

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract It is very attractive yet underexplored to synthesize heterocyclic moieties pertaining to biologically active molecules from biomass-based starting compounds. Herein, we report an electrocatalytic Achmatowicz reaction for the synthesis of hydropyranones from furfuryl alcohols, which can be readily produced from biomass-derived and industrially available furfural. Taking advantage of photo-induced polymerization of a bipyridyl ligand, we demonstrate the facile preparation of a heterogenized nickel electrocatalyst, which effectively drives the Achmatowicz reaction electrochemically. A suite of characterization techniques and density functional theory computations were performed to aid the understanding of the reaction mechanism. It is rationalized that the unsaturated coordination sphere of nickel sites in our electrocatalyst plays an important role at low applied potential, not only allowing the intimate interaction between the nickel center and furfuryl alcohol but also enabling the transfer of hydroxide from nickel to the bound furfuryl alcohol.

Date: 2021
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DOI: 10.1038/s41467-021-22157-5

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