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

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• 作者：Subbiah Sowmiah ; Lu铆s F. Veiros ; Jos茅 M. S. S. Esperan莽a ; Lu铆s P.N. Rebelo ; Carlos A. M. Afonso
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5244-5247
• 全文大小：349K
• ISSN：1523-7052

文摘

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.