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

Matea Vlatkovic; Ben L. Feringa

doi:10.1016/j.tet.2019.02.035

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 journal › Article › Academic › peer-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 language	English
Pages (from-to)	2188-2192
Number of pages	5
Journal	Tetrahedron
Volume	75
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2019.02.035
Publication status	Published - 5-Apr-2019

Keywords

Thioureas
Unclicking of thioureas
Base catalyzed elimination

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Unclicking of thioureas: Base catalyzed elimination of anilines and isothiocyanates from thioureas
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T2 - Base catalyzed elimination of anilines and isothiocyanates from thioureas

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AU - Feringa, Ben L.

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N2 - 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.

AB - 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.

KW - Thioureas

KW - Unclicking of thioureas

KW - Base catalyzed elimination

U2 - 10.1016/j.tet.2019.02.035

DO - 10.1016/j.tet.2019.02.035

M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

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