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Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent

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Abstract

Thioformamides are easily prepared – under full chemocontrol – through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent. The high electrophilicity of the starting materials enables the straightforward addition of the hydride ion, thus constituting a reliable and high-yielding method for obtaining variously functionalized thioformamides. Sensitive chemical groups to the reduction conditions such as nitro, ester, alkene, azo, azide and keto groups do not interfere with the chemoselectivity of the process. Moreover, the stereochemical information embodied in the starting material is fully retained in the final products. The synthetic potential of the selected thioformamide template is also briefly discussed.

Graphical abstract: Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent

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Publication details

The article was received on 18 Sep 2018, accepted on 22 Oct 2018 and first published on 22 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02312C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent

    K. de la Vega-Hernández, R. Senatore, M. Miele, E. Urban, W. Holzer and V. Pace, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02312C

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