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Identifier

000416550

Title

Φορμυλίωση αλκοολών και αμινών μέσω αεροβικής οξειδωτικής σύζευξης με φορμαλδεύδη καταλυόμενη από νανοσωματίδια χρυσού

Alternative Title

Formylation of alcohols and amines via aerobic oxidative coupling with for-maldehyde catalysed by gold nanoparticles

Author

Μεταξάς, Ιωάννης Μ.

Thesis advisor

Στρατάκης, Μανώλης

Reviewer

Σμόνου, Ιουλία
Βασιλικογιαννάκης, Γεώργιος

Abstract

In the present scientific dissertation two simple protocols for the synthesis of formate esters and formamides with aerobic coupling between alcohols or amines with formaldehyde catalyzed by Au/TiO₂ are presented. The suitable form of formaldehyde is paraformaldehyde, as the trimeric 1,3,5-trioxane is inactive under the reaction’s conditions. The reaction’s mechanism proceeds through the formation of a hemiacetal or hemiaminal intermediate, respectively, followed by it’s aerobic oxidation catalyzed by Au nanoparticles. For the alcohols the oxidative coupling with paraformaldehyde is unprecedented. Typically 3 equivalents of paraformaldehyde are required and heating to 80 ^οC with reaction times ranging from 10 to 24 h. Typically for the amines the oxidative coupling with paraformaldehyde requires 4-5 h in room temperature with 2-3 equivalents of paraformaldehyde. Adition of base is not necessary in contrast with analogous coupling reactions in the literature. The catalyst is recyclable and can be reused after a simple filtration up to 5 consecutive runs with a small loss of activity.

Language

Greek

Subject

Aerobic coupling

Au nanoparticles

Formamides

Formates

Paraformaldehyde

Αεροβική σύζευξη

Νανοσωματίδια χρυσού

Παραφορμαλδεΰδη

Φορμαμίδια