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Selectfluor-Promoted Reactions of Aryl Methyl Ketones with Dimethyl Sulfoxide to Give 2,5-Diacylthiophenes and β-Acyl Allylic Methylsulfones

Hao Lu, Jiayi Chen, Wenjun Zhou, Lifen Peng*, Shuang-Feng Yin, Nobuaki Kambe and Renhua Qiu*

*College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China, Email: renhuaqiu1hnu.edu.cn

H. Lu, J. Chen, W. Zhou, L. Peng, S.-F. Yin, N. Kambe, R. Qiu, Org. Lett., 2023, 25, 389-394.

DOI: 10.1021/acs.orglett.2c04101


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Abstract

Selectfluor-promoted cascade cyclizations and cross-coupling reactions provide either 2,5-diacylthiophenes or β-acyl allylic methylsulfones from readily available starting materials by simple solvent modification. The transformations offer excellent chemoselectivity, and good functional group tolerance.

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proposed mechanism



General procedure: Preparation of β-acyl allylic methylsulfones

Weight aryl kethyl ketone (0.25 mmol) and Selectfluor (0.5 mmol, 2 equiv) in a 10.0 mL reaction tube equipped with a magnetic stir bar, and then inject 1.75 mL of anhydrous DMSO and 0.25 mL of anhydrous MePh. The reaction solution was heated to 120 C and in an oil bath stirred for 12 hours under nitrogen. After the reaction finished, the reaction mixture was cooled to room temperature, and the aqueous phase was extracted 3 times with ethylacetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether/EtOAc as the eluent to give β-acyl allylic methylsulfones.


Key Words

sulfones, enones, oxidation, selectfluor


ID: J54-Y2023