Organocatalyzed One-Step Synthesis of Functionalized N-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

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

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 H218O isotope labeled experiments showing no incorporation of 18O in the product.

Original languageEnglish
Pages (from-to)5244-5247
Number of pages4
JournalOrganic Letters
Volume17
Issue number21
DOIs
Publication statusPublished - 6 Nov 2015

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