Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide

Abstract

The catalytic potential of a series of ammonium halide salts was explored in the coupling reaction of a model aziridine with carbon dioxide, highlighting the superior activity of [NH2Et2]I. Then,...

Ammonium Ferrate‐Catalyzed Cycloaddition of CO2 to Aziridines for the Synthesis of 1,3‐Oxazolidin‐2‐ones

“…The synthesis and characterization of the ammonium ferrates and the employed aziridines, as well as the full characterization of 1,3-oxazolidin-2-ones 2 a-o and piperazines 3 a, 3 a' and 3 k are detailed in the Supporting information. The collected data for 1,3-oxazolidin-2-ones are in accordance with those reported in literature: 2 a, 2 b, 2 h, 2 i and 2 j; [42] 2 c; [57] 2 d and 2 e; [31] 2 f and 2 g; [38] 2 k; [29] 2 l, [53] 2 n, [58] 2 o. [59] General catalytic procedure.…”

“…[25] Another 100 % atom-economic process is represented by the cycloaddition reaction of CO 2 to aziridines that occurs at very high temperatures and pressures. [26][27][28] This reaction can be efficiently promoted by several homogeneous [29][30][31][32] and heterogeneous [33][34][35][36][37][38] catalysts by applying more sustainable conditions such as lower temperatures and lower CO 2 pressures. Related 5-hydroxymethyl-substituted 1,3-oxazlidin-2-ones can be efficiently obtained by the cycloaddition reaction of CO 2 to epoxyamines.…”

Protonated Porphyrins: Bifunctional Catalysts for the Metal‐Free Synthesis of N‐Alkyl‐Oxazolidinones

“…Even if ammonium salts,[ 26 , 27 ] ionic liquids[ 28 , 29 ] N‐heterocyclic olefins [30] can be used alone to promote the reaction of aziridines with CO 2 , catalytic performances usually enhance in the presence of binary systems[ 28 , 30 , 31 , 32 , 33 , 34 ] constituted by an electrophilic (E) and nucleophilic (Nu) species, which play synergic roles in optimizing the catalytic efficiency as well as improving the reaction regioselectivity. As reported in Scheme 1 , the reaction can form the two regioisomers A and B and the nature of the electrophilic species is fundamental to drive the nucleophilic attack to the aziridine ring and maximize the reaction regioselectivity.…”

Highly Efficient Conversion of Aziridines and CO2 Catalyzed by Microporous [Cu12] Nanocages

“…As a result, many efficient catalysts were developed for this reaction and exhibit good catalytic performance. For example, [NH 2 Et 2 ]­I, ZrOCl 2 ·8H 2 O, alkali metal halide, ionic liquids, and metal complexes , have been exploited for the conversion of CO 2 with aziridines. Although great progress has been made, most of these catalytic systems are associated with low TON values (<60) and involve in addition toxic solvents or homogeneous catalysts.…”