Unclicking of thioureas: Base catalyzed elimination of anilines and isothiocyanates from thioureas

Matea Vlatkovic, Ben L. Feringa*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

Abstract

Bisaromatic thioureas are widely used in e.g. asymmetric organocatalysis and considered to be robust compounds. Herein we show, in strong contrast to common notion, that thioureas dissociate to amines and isothiocyanates in a base catalyzed reaction under mild conditions. This 'unclicking' process can occur in the presence of weak organic bases even at moderate temperatures. The influence of the substituents at the aromatic rings of the thiourea on the regioselectivity of this unclicking process is also shown. (C) 2019 Published by Elsevier Ltd.

Original languageEnglish
Pages (from-to)2188-2192
Number of pages5
JournalTetrahedron
Volume75
Issue number14
DOIs
Publication statusPublished - 5-Apr-2019

Keywords

  • Thioureas
  • Unclicking of thioureas
  • Base catalyzed elimination

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