Abstract
The presence of sulfur–carbon bonds is transversal to several areas of chemistry, e.g., drug discovery, materials, and chemical biology. However, a lack of efficient and sustainable procedures for the preparation of thioaminals, the N,S-analogues of O,O-acetals, contributes to this functional group often being overlooked by the scientific community. In this work is described the formation of thioaminals in water promoted by copper(II) triflate.
Highlights
The preparation of sulfur-rich frameworks has been a relevant topic for organic chemists, given its importance in materials [1–4] and medicinal chemistry [5,6]
High-Resolution Mass Spectrometry (HRMS) results were recorded in a Thermo Scientific Q Exactive hybrid quadrupole-Orbitrap mass spectrometer (Thermo ScientificTM Q ExactiveTM Plus, Waltham, Massachusetts, U.S.). 1H NMR, 13C NMR, HRMS and melting-point data are reported for all new compounds
Aldehyde (0.942 mmol, 1 equiv) and morpholine (0.942 mmol, 1 equiv) were placed in a round-bottom flask followed by addition of aqueous stock solution of Cu(OTf)2 (1 mol%, 227 μL from 15 mg/mL stock solution)
Summary
The preparation of sulfur-rich frameworks has been a relevant topic for organic chemists, given its importance in materials [1–4] and medicinal chemistry [5,6]. There has been an increased concern about the development of sustainable methodologies [24–27], including procedures in water [28–32] With this in mind, our group (i) focused on the valorization of raw renewable materials such as furfural and hydroxymethylfurfural (HMF) [33–35] and (ii) reported on the use of water as a green reaction media for the production of cyclopentenones [36] and, more recently, aminals from the condensation of aryl aldehydes with amines [37]. Our group (i) focused on the valorization of raw renewable materials such as furfural and hydroxymethylfurfural (HMF) [33–35] and (ii) reported on the use of water as a green reaction media for the production of cyclopentenones [36] and, more recently, aminals from the condensation of aryl aldehydes with amines [37] This addresses one of the 12 principles of green chemistry [24], namely the use of less hazardous/toxic chemicals.
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