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; Renhua Qiu

doi:10.1021/acs.orglett.2c04101

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

Org Lett. 2023 Jan 20;25(2):389-394. doi: 10.1021/acs.orglett.2c04101. Epub 2023 Jan 6.

Authors

Hao Lu¹, Jiayi Chen², Wenjun Zhou¹, Lifen Peng², Shuang-Feng Yin¹, Nobuaki Kambe^{1

3}, Renhua Qiu¹

Affiliations

¹ State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China.
² Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201, China.
³ The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.

PMID: 36607146
DOI: 10.1021/acs.orglett.2c04101

Abstract

In this paper, a convenient synthesis of 2,5-diacylthiophenes and β-acyl allylic methylsulfones from aryl methyl ketones with dimethyl sulfoxide (DMSO) through Selectfluor-promoted cascade cyclization and cross-coupling reactions by simple solvent modification is described. This method enables the formation of new C-C and C-S bonds via the selection of different solvent ratios, in which DMSO molecules as synthons can be selectively introduced into methyl ketones. The features of this transformation include readily available starting materials, excellent chemoselectivity, and good functional group tolerance.