Synthesis of 3-Phenylsulfonylcoumarins by Cyclisation of Phenyl Propiolates with Sulfinic Acids or Sodium Sulfinates

Methods for the synthesis of 3-phenylsulfonylcoumarins by radical sulfonylation cyclisation of phenyl propiolates with sulfinic acids or sodium sulfinates as sulfonyl sources have been developed. A combination of potassium persulfate as oxidant and silver nitrate as catalyst, or tert-butyl hydroperoxide as oxidant and potassium iodide as catalyst were used. The products were formed by an ipso-cyclisation/1,2-ester migration mechanism. The toleration of functional groups is broad and the yield is up to 96%.