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

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 str...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-02, Vol.7 (3), p.563-570
Main Authors: Yan-Ling, Ji, Xiang-Hong, He, Guo, Li, Yue-Yan, Ai, He-Ping, Li, Cheng, Peng, Han, Bo
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Alkenes
Chemical reactions
Crystallography
Functional groups
Organic chemistry
Regioselectivity
Substrates
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo01436e