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