Organocatalyzed One-Step Synthesis of Functionalized N-Alkyl-Pyridinium Salts from Biomass Derived 5‑Hydroxymethylfurfural

An efficient and scalable method has been developed for the synthesis of N-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-N-alky...

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Published inOrganic letters Vol. 17; no. 21; pp. 5244 - 5247
Main Authors Sowmiah, Subbiah, Veiros, Luís F, Esperança, José M. S. S, Rebelo, Luís P.N, Afonso, Carlos A. M
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 06.11.2015
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Summary:An efficient and scalable method has been developed for the synthesis of N-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-N-alkylpyridinium salts. In addition, the mechanism for the formation of pyridinium salts was studied by DFT and using H2 18O isotope labeled experiments showing no incorporation of 18O in the product.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02573