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.

Organometallic Approaches to Carbon–Sulfur Bond Formation

“…Similarly, Cu-catalyzed coupling of arylboronic acids with sulfinate anions has been reported [95,149,150]. Notably, Kantam and co-workers found that the use of ionic liquids permits Cu(OAc) 2 -catalyzed sulfone synthesis at ambient temperature and with convenient product separation and catalyst recyclability (17) [150]. …”

“…More recently, both Cu-and Pd-catalyzed couplings of sulfinate anions with aryl halides have also been reported as a means to generate unsymmetrical diaryl sulfones, which are common motifs in bioactive molecules [38,93,[144][145][146][147][148]. Similarly, Cu-catalyzed coupling of arylboronic acids with sulfinate anions has been reported [95,149,150]. Notably, Kantam and co-workers found that the use of ionic liquids permits Cu(OAc) 2 -catalyzed sulfone synthesis at ambient temperature and with convenient product separation and catalyst recyclability (17) [150].…”

“…Ionic liquids as solvents for sulfinate ion cross-couplings [150] 3 Reactions of Sulfur-Containing Reagents Across p-Bonds…”

Imidazolium Ionic Liquids: An Environment-Friendly Medium for Various Applications

“…Urea-hydrogen peroxide in the presence of catalytic amount of magnesium bromide efficiently oxidizes primary and secondary benzylic alcohols into the corresponding aromatic aldehydes and ketones [30] [34]. M. L. Kantam et al described copper-catalyzed cross-coupling reaction of arylboronic acids with sulfonic acid for alkylaryl and diaryl sulfones using IL [35].…”

The Formation of Csp 2 S and Csp 2 Se Bonds by Substitution and Addition Reactions Catalyzed by Transition Metal Complexes

“…In ionic liquid it was possible to carry out oxidative coupling of aryl boronic acid with the sodium salt of sulfonic acid (Scheme 3.53) [92].…”