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

Chun-Lin Zhang, Zhao-Fei Zhang, Zi-Hao Xia, You-Feng Han, Song Ye*

*Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China, Email: songyeiccas.ac.cn

C.-L. Zhang, Z.-F. Zhang, Z.-H. Xia, Y.-F. Han, S. Ye, J. Org. Chem., 2018, 83, 12507-12513.

DOI: 10.1021/acs.joc.8b01740 (free Supporting Information)


Abstract

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


see article for more examples



N-Heterocyclic Carbene-Catalyzed Construction of 1,3,5-Trisubstituted Benzenes from Bromoenals and α-Cyano-β-methylenones

C.-L. Zhang, S. Ye, Org. Lett., 2016, 18, 6408-6411.


Key Words

cyclization


ID: J42-Y2018