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One-Pot, Three-Component Assembly of Sulfides Using a Sulfoxide Reagent as a Sulfur Dication Equivalent

Fumito Saito* and Simon Euteneuer

*Department of Chemistry, Ludwig Maximilian University, Butenandtstr. 5−13, 81377 Munich, Germany, Email: fumito.saitocup.uni-muenchen.de

F. Saito, S. Euteneuer, Org. Lett., 2023, 25, 6057-6061.

DOI: 10.1021/acs.orglett.3c02301


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Abstract

A one-pot, three-component synthesis of sulfides uses a sulfoxide reagent as a formal sulfur dication equivalent. Three simple chemical operations involving two Grignard reagents and trimethylsilyl chloride (TMSCl) sequentially form sulfenate anions, sulfenate esters, and sulfides. A wide range of Grignard reagents can be coupled, thereby allowing a modular, thiol-free synthesis of sulfides.

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Synthesis of Sulfides

The sulfoxide reagent (126 mg, 0.50 mmol, 1.0 equiv) was dissolved in THF (5.0 mL) at room temperature. The solution was cooled to the specified temperature. A solution of the specified Grignard reagent (0.50 mmol, 1.0 equiv) was added dropwise, and the resulting mixture was stirred at this temperature for the specified time. The reaction was cooled to -78C, and trimethylsilyl chloride (95 L, 0.75 mmol, 1.5 equiv) was added dropwise. The resulting mixture was stirred at the same temperature for 30 min, followed by the addition of a 1.0 M solution of o-methoxyphenylmagnesium bromide in THF (0.75 mL, 0.75 mmol, 1.5 equiv) in one portion. The mixture was warmed to room temperature and stirred at this temperature for the specified time. The reaction was quenched with sat aq NH4Cl and diluted with EtOAc and H2O. The two phases were separated, and the aqueous phase was extracted with EtOAc (2x). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford the desired product.


Key Words

aryl sulfides


ID: J54-Y2023