Organocatalyzed One-Step Synthesis of Functionalized <i>N-</i>Alkyl-Pyridinium Salts from Biomass Derived 5‑Hydroxymethylfurfural Subbiah Sowmiah Luís F. Veiros José M. S. S. Esperança Luís P.N. Rebelo Carlos A. M. Afonso 10.1021/acs.orglett.5b02573.s001 https://acs.figshare.com/articles/journal_contribution/Organocatalyzed_One_Step_Synthesis_of_Functionalized_i_N_i_Alkyl_Pyridinium_Salts_from_Biomass_Derived_5_Hydroxymethylfurfural/2112247 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. 2015-11-06 00:00:00 formic acid alkyl amines DFT 18 O scalable method formation H 218O isotope pyridinium salts