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

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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… Click to show full 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.

Keywords: ketones dimethyl; aryl methyl; diacylthiophenes acyl; acyl allylic; allylic methylsulfones; methyl ketones

Journal Title: Organic letters
Year Published: 2023

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