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

doi:10.1021/acs.orglett.5b02573

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

Org Lett. 2015 Nov 6;17(21):5244-7. doi: 10.1021/acs.orglett.5b02573. Epub 2015 Oct 23.

Authors

Subbiah Sowmiah^{1

2}, Luís F Veiros³, José M S S Esperança¹, Luís P N Rebelo¹, Carlos A M Afonso²

Affiliations

¹ Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa , Av. da República, 2780-157 Oeiras, Portugal.
² iMed. UL, Faculdade de Farmácia da Universidade de Lisboa , Av. Prof. Gama Pinto, 1640-003 Lisboa, Portugal.
³ Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Universidade de Lisboa , Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal.

PMID: 26493742
DOI: 10.1021/acs.orglett.5b02573

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 H2(18)O isotope labeled experiments showing no incorporation of (18)O in the product.

Publication types

Research Support, Non-U.S. Gov't