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Synthesis 2018; 50(15): 3031-3040
DOI: 10.1055/s-0037-1610179
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© Georg Thieme Verlag Stuttgart · New York

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

Patricia Gisbert
Organic Chemistry Department and Instituto de Síntesis Orgánica (ISO), University of Alicante, Apdo. 99, 03080 Alicante, Spain   Email: ipastor@ua.es
,
Isidro M. Pastor  *
Organic Chemistry Department and Instituto de Síntesis Orgánica (ISO), University of Alicante, Apdo. 99, 03080 Alicante, Spain   Email: ipastor@ua.es
› Author AffiliationsThis work was financially supported by the Spanish Ministry (Ministerio de Economía y Competitividad CTQ2015-66624-P) and the University of Alicante (VIGROB-285).
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Publication History

Received: 25 April 2018

Accepted: 11 May 2018

Publication Date:
02 July 2018 (online)

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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.

Key words

imidazolium salt - ionic liquid - iron(III) catalyst - sulfur - thioamides

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    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610179.
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