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