Organocatalyzed One-Step Synthesis of Functionalized N-AlkylPyridinium 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-alkyl...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 21; pp. 5244 - 5247
Main Authors Sowmiah, Subbiah, Veiros, Luis F., Esperanca, Jose M. S. S., Rebelo, Luis P. N., Afonso, Carlos A. M.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 06.11.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDROGENATION
PYRIDINIUM SALTS
ALKALOIDS
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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 (H2O)-O-18 isotope labeled experiments showing no incorporation of O-18 in the product.
Bibliography:FCT
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02573