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Transition-Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts

Hao Yu, Zhen Li, Carsten Bolm*

*Institute of Organic Chemistry, RWTH Aachen University Landoltweg 1, 52074 Aachen, Germany, Email: carsten.bolmoc.rwth-aachen

H. Yu, Z. Li, C. Bolm, Org. Lett., 2018, 20, 7104-7106.

DOI: 10.1021/acs.orglett.8b03046



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Abstract

A mild transition-metal-free arylation of sulfenate anions generated from β-sulfinyl esters with diaryliodonium salts provides a wide range of S,S-diaryl and S-alkyl S-aryl sulfoxides.

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General Procedure:

In a 10 mL sealed tube under argon was successively added β-sulfinyl esters (0.2 mmol, 1.0 equiv), diaryliodonium salts (0.22 mmol, 1.1 equiv) and a mixture of toluene (1 mL) and H2O (1 mL). Then, a 50% aqueous KOH solution (4.0 mmol, 20.0 equiv) was added dropwise. The resulting turbid reaction mixture was stirred at room temperature for 24 h and then quenched by the addition of a 1M aqueous HCl solution (5 mL). After addition of water (5 mL) and extraction with CH2Cl2 (3 10 mL), the combined organic layers were dried over MgSO4, filtered and concentrated. The product was purified by column chromatography on silica gel to afford the desired sulfoxides.


Key Words

aryl sulfones


ID: J54-Y2018