Aerobic α‐Sulfonylation of Ketones with Zinc Sulfinates in Aqueous Micellar Media: Highly Selective Access to β‐Keto Sulfones

Abstract

AbstractAn efficient, inexpensive and environmentally friendly synthesis of β‐ketosulfones, via NaI‐catalyzed oxidative sulfonylation of ketones with zinc sulfinates, employing ethylene dibromide (EDB) and air as the oxidants, is described. EDB was shown to be a mild organic oxidant to convert NaI into molecular iodine that promote the cross‐coupling reactions of zinc sulfinates with ketones, producing β‐ketosulfones. Mechanistic studies indicated that a radical pathway might be involved in the reaction process. The key feature of the present protocol is the far greater solubility of NaI and sulfinates in micellar arrays present in aqueous solution where the oxidative coupling reactions are taking place.