Reactions with vinyliodonium salts generally lead to the monofunctionalization of nucleophiles or fragmentation to vinyl iodides, and vinylbenziodoxolones (VBX) were recently reported as a related reagent class. In contrast to reactions with ethynylbenziodoxolones (EBX), it should be noted that difunctionalizations using vinyliodonium salts or VBX remain unreported. When the aryl(vinyl)iodonium salt 4a(OTf) was reacted with 2d under the diarylation conditions, only 21% of the desired product 5a was observed, with 8:1 E:Z selectivity (Table , entry 1). Reactions with potassium thioacetate 2c afforded 5a 3ag 86% Ph S