Assembly of 3-sulfonated 2H-pyrrol-2-ones through the insertion of sulfur dioxide with allenoic amides

Abstract

Generation of 3-sulfonated 2H-pyrrol-2-ones through a three-component reaction of allenoic amides, sulfur dioxide, and aryldiazonium tetrafluoroborates under metal-free conditions is achieved. This transformation proceeds under mild conditions without the addition of catalysts or additives, giving rise to 3-sulfonated 2H-pyrrol-2-ones in moderate to good yields. Good functional group compatibility is observed. A plausible mechanism is proposed, which is initiated by aryl radicals formed in situ from aryldiazonium tetrafluoroborates and DABCO·(SO2)2. Additionally, excellent chemoselectivity and regioselectivity are presented in this transformation.