Sulfonylation and Phosphinylation of Olefinic Compounds with Radical Species Generated by the Oxidation of Sodium Sulfinates and Diphenylphosphine Oxide

Sodium arenesulfinates are oxidized with manganese(III) 2-pyridinecarboxylate or ammonium cerium(IV) nitrates to generate sulfonyl radicals, which add to olefinic compounds to afford sulfonylated products in good yield. When 1-vinyl cyclic alcohols are used as sulfonyl radical acceptors, sulfonylation proceeds with ring-enlargement. Diphenylphosphinyl radical can also be generated by treating diphenylphosphine oxide with manganese(III) 2-pyridinecarboxylate and reacts with olefinic compounds, giving phosphinylated products.