HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media
- 11 October 2021
- journal article
- research article
- Published by Taylor & Francis Ltd in Synthetic Communications
- Vol. 51 (24), 3729-3739
- https://doi.org/10.1080/00397911.2021.1989597
Abstract
We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and purification. Notably, this approach conventionally used to synthesize molecules on gram scales with excellent yields and a high tolerance for functional groups. Graphical AbstractKeywords
This publication has 25 references indexed in Scilit:
- Synthesis of Mesoporous Cerium Oxide (CeO2) Nanoparticles and Effect of Cerium Precursors on Transamidation of Acetamide with N-Octylamine Under Solvent-Free ConditionsJournal of Nanoscience and Nanotechnology, 2017
- A General Method for Two-Step Transamidation of Secondary Amides Using Commercially Available, Air- and Moisture-Stable Palladium/NHC (N-Heterocyclic Carbene) ComplexesOrganic Letters, 2017
- Nickel-(II)-Catalyzed N-Formylation and N-Acylation of AminesOrganic Letters, 2017
- A two-step approach to achieve secondary amide transamidation enabled by nickel catalysisNature Communications, 2016
- Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild ConditionsChemistry – A European Journal, 2016
- A metal-free approach for transamidation of amides with amines in aqueous mediaTetrahedron Letters, 2015
- Sulphuric acid immobilized on silica gel (H2SO4–SiO2) as an eco-friendly catalyst for transamidationRSC Advances, 2015
- A convenient procedure for N-formylation of aminesTetrahedron Letters, 2013
- Efficient Copper(II)‐Catalyzed Transamidation of Non‐Activated Primary Carboxamides and Ureas with AminesAngewandte Chemie, 2012
- Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic CatalystAngewandte Chemie, 2011