Combined experimental and computational study of Al₂O₃ catalyzed transamidation of secondary amides with amines

Abstract

Amides are the most extensively used substances in both synthetic organic and bioorganic chemistry.

A Novel Approach of Electrocatalytic Deamination From Aromatic Amide to Diarylimide on Ni‐PTFE Modified Electrode

“…The reduction of aromatic amide is a one‐electron transfer process, and one molecule of product was generated. Along with H 2 generation with one molecule, [40–43] the electrocatalytic reduction from aromatic amide to diarylimide is consistent with two electroreduction processes in wholly.…”

“…It is adsorbed on the electrode surface by hydrophobic bonding forces. Secondly, an Along with H 2 generation with one molecule, [40][41][42][43] the electrocatalytic reduction from aromatic amide to diarylimide is consistent with two electroreduction processes in wholly.…”

Transamidation vitrimers enabled by neighbouring fluorine atom activation

“…The computations used the same methodology (functional, basis sets and various corrections, see details in the Experimental section) as our previously published study of the F substitution effect on the transesterification rate. 78 The literature reports only a few DFT investigations of the transamidation reaction mechanism, mostly restricted to metalcatalyzed 53,82,83 or organocatalyzed [84][85][86] processes. It seems that only one report has addressed the non-catalyzed transamidation of a special amide (RCO-NMeOMe, a "Weinreb" amide), in comparison with the CO 2 -catalyzed process.…”

Molecular Oxygen‐Induced Transamidation of Unactivated Amides in Diethyl Carbonate in the Presence of a Palladium Catalyst

“…Stoichiometric amounts of AlCl 3 , [13] N , N ‐carbonyldiimidazole, [14] boric acid, [12d] potassium tert‐butoxide, [15] borate esters, [16] and LiHMDS [12f] can promote the reaction, and in addition to biocatalytic transamidations in the presence of enzymes, [17] several procedures involving an in‐situ activation of the starting amide, [18] those based on ionic liquid catalysts [19] and even a catalyst‐free procedure [20] have been reported. Moreover, the use of catalytic amounts (5–50 mol%) of bisacetoxyiodobenzene, [21] povidone iodine, [22] hydroxylamine hydrochloride, [23] benzoic acid, [24] L‐proline,, [25] chitosan, [26] benzotriazole, [27] SiO 2 −H 2 SO 4 and strongly acidic mesoporous silica, [28] H‐β‐zeolite [29] and alumina, [30] inter alia , [31] have been also described in the field of transition metal‐free catalysis. In this regard, a triflic acid‐iodide co‐catalyzed transamidation of unactivated tertiary amides based on an amide re‐routing through reactive acyl iodide intermediates has recently been published [32] …”