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.bolm
oc.rwth-aachen
H. Yu, Z. Li, C. Bolm, Org. Lett., 2018, 20, 7104-7106.
DOI: 10.1021/acs.orglett.8b03046
see article for more reactions
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.
see article for more examples
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
ID: J54-Y2018
