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

Lihong Wang; Ruiyang Ma; Jiuli Xia; Ximin Liu; Jiaqiong Sun; Guangfan Zheng; Qian Zhang

doi:10.1002/chem.202203309

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. 2023 Mar 13;29(15):e202203309. doi: 10.1002/chem.202203309. Epub 2023 Feb 7.

Authors

Lihong Wang¹, Ruiyang Ma¹, Jiuli Xia¹, Ximin Liu¹, Jiaqiong Sun², Guangfan Zheng¹, Qian Zhang^{1

3}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China.
² School of Environment, Northeast Normal University, Changchun 130117, Changchun, 130024, P. R. China.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

PMID: 36509732
DOI: 10.1002/chem.202203309

Abstract

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.

Keywords: 1,3,5-trisubstituted benzene; 6-π electro-cyclization; DBU; allenyl ketones; cascade reaction.

Abstract

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