4.7 Article

DBU-Mediated Construction of 1,3,5-Trisubstituted Benzenes via Annulation of α,β-Unsaturated Carboxylic Acids and α-Cyano-β-methylenones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 20, Pages 12507-12513

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01740

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Funding

  1. National Natural Science Foundation of China [21425207, 21521002]
  2. Chinese Academy of Sciences

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A DBU-mediated synthesis of 1,3,5-trisubstituted benzenes was developed via the [2 + 4] annulation of in situ activated alpha,beta-unsaturated carboxylic acids and alpha-cyano-beta-methylenones. The dual role of DBU as Bronsted base and nucleophilic Lewis base is the key for the success of the reaction.

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