Univerzita Pardubice Fakulta chemicko- technologická

Univerzita Pardubice

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Publikace detail

HYDROGEN CHLORIDE CATALYSED GUANYLATION OF AMINES

Autoři: Vlk Lukáš | Chlupatý Tomáš | Růžička Aleš

Rok: 2022

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	HYDROGEN CHLORIDE CATALYSED GUANYLATION OF AMINES	Guanidines, derivatives of the simplest molecule of Guanidine HN=C(NH2)2, are a class of organic compounds with many industrial applications such as pharmaceuticals, explosives, or sweeteners.1,2 Uses in chemistry include guanidines as basic or/and (non)nucleophilic catalysts,2 polymerization initiators,3 or precursors to guanidinate ligands popular in organometallic chemistry.4 Guanylation of amines employing various guanylating agents (thioureas, isothioureas, cyanamides and others) often requires multiple steps, increased temperature and offers low yields and little versatility.1,2 Modern approaches introduced new, efficient catalysts based on transition metal complexes, generally reaching excellent yields with limited scope of substrates.5 Attempts to discover more affordable catalysts led to usage of metal salts6 and oxides,7 which exhibited lower catalytic efficiency, especially towards less reactive primary and secondary aromatic amines. Here we present an atom-efficient addition of primary aromatic or primary/secondary aliphatic amines to aromatic/aliphatic carbodiimides. This guanylation reaction yields tri- or tetrasubstituted guanidines, respectively, and is catalysed by hydrogen chloride in case of low-reactive substrates. Detailed study of the reaction mechanism is supported by DFT calculations.