期刊
TETRAHEDRON
卷 75, 期 14, 页码 2188-2192出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.02.035
关键词
Thioureas; Unclicking of thioureas; Base catalyzed elimination
资金
- Netherlands Organization for Scientific Research (NWO-CW, Top grant)
- Royal Netherlands Academy of Arts and Sciences (KNAW)
- Ministry of Education, Culture and Science [024.001.035]
- European Research Council [694345]
- European Research Council (ERC) [694345] Funding Source: European Research Council (ERC)
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.
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