Electrocatalytic synthesis of heterocycles from biomass-derived furfuryl alcohols

Liu, Xuan; Li, Bo; Han, Guanqun; Liu, Xingwu; Cao, Zhi; Jiang, De-en; Sun, Yujie

doi:10.1038/s41467-021-22157-5

Title: Electrocatalytic synthesis of heterocycles from biomass-derived furfuryl alcohols

Journal Article · Thu Mar 25 00:00:00 EDT 2021 · Nature Communications

DOI: https://doi.org/10.1038/s41467-021-22157-5 · OSTI ID:1817002

^[1]; Li, Bo ^[2]; Han, Guanqun ^[1]; Liu, Xingwu ^[3]; Cao, Zhi ^[3];

^[2];

^[1]

Univ. of Cincinnati, OH (United States)
Univ. of California, Riverside, CA (United States)
Synfuels China Technology Company, Ltd. (China)

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.

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Research Organization:: Univ. of California, Riverside, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation (NSF); Herman Frasch Foundation

OSTI ID:: 1817002

Journal Information:: Nature Communications, Journal Name: Nature Communications Journal Issue: 1 Vol. 12; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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