Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes

1,3,5-Triaroyl cyclohexane is highly valuable due to its uniqueness of structure.The development of a catalytic and efficient method for the synthesis of 1,3,5-triaroyl cyclohexane is of great value.The cyclotrimerization of chalcones catalyzed by potassium hexamethyldisilazide is described, which effectively produces a series of 1,3,5-triaroyl cyclohexanes in moderate to high yields.A mechanism involving sequential Michael addition catalyzed by silylamide anion is proposed.This method provides a simple, efficient, and atom-economical route for the synthesis of 1,3,5-triaroyl cyclohexanes.

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Publication Details

Journal
Chinese Journal of Organic Chemistry
Published
2025-01-01
DOI
https://doi.org/10.6023/cjoc202408014
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes

Zhigang Yao, Fan Xu, Nana Gao
Chinese Journal of Organic Chemistry
Chemical Synthesis and Analysis
article

Potassium Hexamethyldisilazide-Catalyzed Synthesis of 1,3,5-Triaroyl Cyclohexanes

Zhigang Yao, Fan Xu, Nana Gao
article en

Abstract

1,3,5-Triaroyl cyclohexane is highly valuable due to its uniqueness of structure.The development of a catalytic and efficient method for the synthesis of 1,3,5-triaroyl cyclohexane is of great value.The cyclotrimerization of chalcones catalyzed by potassium hexamethyldisilazide is described, which effectively produces a series of 1,3,5-triaroyl cyclohexanes in moderate to high yields.A mechanism involving sequential Michael addition catalyzed by silylamide anion is proposed.This method provides a simple, efficient, and atom-economical route for the synthesis of 1,3,5-triaroyl cyclohexanes.

Chinese Journal of Organic ChemistryVol. 45(4)
National Key Research and Development Program of China
Openalex Percentile: Top 91%
Chemical Synthesis and Analysis
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