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

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

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Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 20; pp. 12507 - 12513
Main Authors Zhang, Chun-Lin, Zhang, Zhao-Fei, Xia, Zi-Hao, Han, You-Feng, Ye, Song
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.10.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COVALENT ORGANIC FRAMEWORKS
ACTIVATION
DOMINO REACTIONS
ACYLAMMONIUM SALTS
STEREODIVERGENT
COMPLEXES
MULTISUBSTITUTED BENZENES
OXAZOLIDINONES
UMPOLUNG
ORGANOCASCADES
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Summary:A DBU-mediated synthesis of 1,3,5-trisubstituted benzenes was developed via the [2 + 4] annulation of in situ activated α,β-unsaturated carboxylic acids and α-cyano-β-methylenones. The dual role of DBU as Brønsted base and nucleophilic Lewis base is the key for the success of the reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01740