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

Chun-Lin Zhang and 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:

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

DOI: 10.1021/acs.orglett.6b03306 (free Supporting Information)

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A N-heterocyclic carbene-catalyzed [2 + 4] annulation of α-bromoenals and α-cyano-β-methylenones enables a direct and efficient approach to 1,3,5-trisubstituted benzenes. The reaction worked well for both aryl- and alkylenones.

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proposed mechanism

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

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

Key Words

arenes, organocatalysis

ID: J54-Y2016