DBU-Mediated Isomerization/6-π Electro-Cyclization/Oxidation Cascade of Sulfonyl-Substituted Allenyl Ketones for the Construction of Hetero-1,3,5-Trisubstituted Benzene.

Chemistry

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China.

Published: March 2023

1,3,5-tri-substituted benzene rings emerged with unique properties has widespread applications in materials, boosting the rapid development of their synthesis. Despite the significance, the direct construction of hetero-1,3,5-trisubstituted benzene core was far less-developed. Herein, we realized a DBU-mediated isomerization/6-π electro-cyclization/oxidative aromatization cascade of sulfonyl-substituted allenyl ketones under an air atmosphere (DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). This versatile protocol featured metal-free conditions, easy operation, and broad functional group tolerance provides a new avenue for the construction of hetero-1,3,5-tri-substituted benzene.

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Source
http://dx.doi.org/10.1002/chem.202203309DOI Listing

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