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

Subbiah Sowmiah, Luís F. Veiros, José M S S Esperança, Luís P N Rebelo, Carlos A M Afonso

Instituto de Tecnologia Química e Biológica António Xavier (ITQB)

Research output: Contribution to journal › Article › peer-review

32 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 language	English
Pages (from-to)	5244-5247
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.5b02573
Publication status	Published - 6 Nov 2015

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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.",

author = "Subbiah Sowmiah and Veiros, {Lu{\'i}s F.} and Esperan{\c c}a, {Jos{\'e} M S S} and Rebelo, {Lu{\'i}s P N} and Afonso, {Carlos A M}",

year = "2015",

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T1 - Organocatalyzed One-Step Synthesis of Functionalized N-Alkyl-Pyridinium Salts from Biomass Derived 5-Hydroxymethylfurfural

AU - Sowmiah, Subbiah

AU - Veiros, Luís F.

AU - Esperança, José M S S

AU - Rebelo, Luís P N

AU - Afonso, Carlos A M

PY - 2015/11/6

Y1 - 2015/11/6

N2 - 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.

AB - 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.

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ER -

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

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