Organocatalyzed
One-Step Synthesis of Functionalized <i>N-</i>Alkyl-Pyridinium
Salts from Biomass Derived 5‑Hydroxymethylfurfural
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Abstract
An efficient and scalable method
has been developed for the synthesis
of <i>N-</i>alkylpyridinium salts from biomass derived 5-hydroxymethylfurfural
and alkyl amines using a catalytic amount of formic acid. This protocol
is also extended to various diamines providing the exclusive formation
of mono-<i>N-</i>alkylpyridinium salts. In addition, the
mechanism for the formation of pyridinium salts was studied by DFT
and using H<sub>2</sub><sup>18</sup>O isotope labeled experiments
showing no incorporation of <sup>18</sup>O in the product