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Substrate-directed chemo- and regioselective synthesis of polyfunctionalized trifluoromethylarenes via organocatalytic benzannulation

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Abstract

Highly chemo- and regioselective substrate-directed benzannulation of trisubstituted CF3-alkenes and 2-benzylidenemalononitriles or 2-nitroallylic acetates has been achieved via Michael-initiated [4 + 2] or Rauhut–Currier-initiated [3 + 3] annulation. These protocols enable the rapid assembly of structurally important tri-fluoromethylarene cores featuring five or four contiguous functional groups, affording a broad spectrum of products with diverse substituents in generally high yields. These products could be facilely transformed into structurally diverse molecules of synthetic and medicinal interest.

Graphical abstract: Substrate-directed chemo- and regioselective synthesis of polyfunctionalized trifluoromethylarenes via organocatalytic benzannulation

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Article information


Submitted
01 Dec 2019
Accepted
28 Dec 2019
First published
30 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Substrate-directed chemo- and regioselective synthesis of polyfunctionalized trifluoromethylarenes via organocatalytic benzannulation

Y. Ji, X. He, G. Li, Y. Ai, H. Li, C. Peng and B. Han, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01436E

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