Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water

ABATRACT

A direct approach to N,N′-disubstituted urea/thiourea from the self-condensation reactions of isothiocyanates in water has been developed. This access tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to N,N′-disubstituted urea/thiourea in moderate to excellent yields from safe and easily available starting materials. A plausible mechanism of the desulfurization self-condensation reaction for urea was also proposed and the role of di-tert-butyl peroxide (DTBP) and copper catalyst in the present strategy was demonstrated with the help of ESI mass spectrometry of intermediate studies.

Graphical Abstract

DTBP-mediated synthesis of N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water

Keywords:

• Desulfurization self-condensation
• DTBP
• N,N′-disubstituted urea/thiourea
• water

Disclosure statement

There are no conflicts of interest to declare.

Additional information

Funding

This work was supported by the National Natural Science Foundation of China (21102132 and 21172200).