Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 2019
Previous Article Next Article

Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
18 Sep 2018
Accepted
22 Oct 2018
First published
22 Oct 2018

Org. Biomol. Chem., 2019,17, 1970-1978
Article type
Paper

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., 2019, 17, 1970
DOI: 10.1039/C8OB02312C

Social activity

Search articles by author

Spotlight

Advertisements