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Selective Conversion of Furoic Acid Derivatives to Multi‐Substituted Furanacrylate by a Ruthenium Catalyst

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Furanacrylate derivatives, as a class of multi‐substituted furan compounds, have been widely used in drug synthesis, organic functional materials, novel polymer monomers, etc. In this paper, direct alkenylation and decarboxylation‐alkenylation… Click to show full abstract

Furanacrylate derivatives, as a class of multi‐substituted furan compounds, have been widely used in drug synthesis, organic functional materials, novel polymer monomers, etc. In this paper, direct alkenylation and decarboxylation‐alkenylation of furoic acid derivatives to furanacrylate were carried out by efficient [Ru(p‐cymene)Cl2]2 catalyst. The effects of reaction parameters on product distribution were investigated and discussed in detail. Up to 76 % and 80 % isolated yield of furanacrylate by direct alkenylation and decarboxylation‐alkenylation of furoic acid derivatives were obtained at 80 °C and 125 °C, respectively. A good substrate compatibility was disclosed through the screening of substrate scope. Meanwhile, Ru(II) or Cu(II) was essential for decarboxylation according to the control experiments. This opened a new general route from biomass‐derived compounds to functionalized multi‐substituted furan compounds.

Keywords: alkenylation; furoic acid; multi substituted; acid derivatives

Journal Title: ChemCatChem
Year Published: 2019

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