Oxidative Coupling–Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides

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Title: Oxidative Coupling–Thionation of Amines Mediated by Iron-Based Imidazolium Salts for the Preparation of Thioamides
Authors: Gisbert, Patricia | Pastor, Isidro M.
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Imidazolium salt | Ionic liquid | Iron(III) catalyst | Sulfur | Thioamides
Knowledge Area: Química Orgánica
Issue Date: 2-Jul-2018
Publisher: Georg Thieme Verlag
Citation: Synthesis. 2018, 50(15): 3031-3040. doi:10.1055/s-0037-1610179
Abstract: An efficient and selective multicomponent oxidative coupling, involving the use of two different amines, sodium phosphate, and elemental sulfur have been described for the preparation of thioamides, employing microwave irradiation. The use of an iron(III)-based imidazolium salt is essential as catalyst. Indeed, the iron-based catalyst is involved in the oxidative coupling of the two amines and in the subsequent C–S bond formation. The protocol is useful for a wide variety of primary benzylamines and alkylamines, as coupling partners. Thus, various electron-rich and electron-poor substituents in the aromatic rings and also fused piperidine derivatives, are suitable starting materials in this reaction. Some of the obtained products are important synthetic intermediates for natural products.
Sponsor: This work was financially supported by the Spanish Ministry (Ministerio de Economía y Competitividad CTQ2015-66624-P) and the University of Alicante (VIGROB-285).
URI: http://hdl.handle.net/10045/77778
ISSN: 0039-7881 (Print) | 1437-210X (Online)
DOI: 10.1055/s-0037-1610179
Language: eng
Type: info:eu-repo/semantics/article
Rights: © Georg Thieme Verlag Stuttgart · New York
Peer Review: si
Publisher version: https://doi.org/10.1055/s-0037-1610179
Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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