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

Author:
Vlatković, Matea, Feringa, Ben L.
Source:
Tetrahedron 2019 v.75 no.14 pp. 2188-2192
ISSN:
0040-4020
Subject:
amines, aromatic compounds, catalytic activity, chemical reactions, chemical structure, isothiocyanates, regioselectivity, temperature, thiourea
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.
Agid:
6328747