Copper-Catalyzed Sulfonylation of Arylboronic Acids in Ionic Liquids

Abstract

Cupric acetate in ionic liquids (ILs) catalyzes coupling reaction of arylboronic acids with sulfinic acid salts to afford aryl sulfones in good yields under ambient conditions. This mild and efficient cross-coupling reaction gives access to a wide range of al­kylaryl and diaryl sulfones in good yields. The use of ionic liquid allows for easy separation of the product and recycling of copper catalyst.

Key words

aryl sulfones - cupric acetate - ionic liquids - recyclability

References and Notes

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18

Ionic liquids were synthesized according to the procedures reported in the literature and their purity was confirmed by ¹H NMR and TGA-DTA analysis.¹⁹
General Procedure for the Preparation of Sulfones: To a solution of Cu(OAc)₂ (0.013 g, 10 mol%) in ionic liquid (1 mL) and arylboronic acid (1 mmol), sodium sulfinate salt (1 mmol) was added and stirred at r.t. for 12 h. After completion of the reaction, as monitored by TLC, the crude product was extracted with Et₂O (3 × 10 mL). The combined Et₂O extracts were concentrated in vacuo and the resulting product was purified by column chromatography on silica gel with EtOAc-n-hexane (2:8) as eluent to afford the desired product. The products were characterized by comparison of their NMR and mass spectra with those reported in the literature.^12c,14 The ionic liquid containing Cu(OAc)₂ was dried under vacuum and preserved for the next run.