Iodoarenes 1 were readily oxidized to (diacetoxyiodo)arenes 8 with sodium hypochlorite under acidic conditions. Careful regulation of the reaction time is instrumental for the success of the reaction. We found that reactions times of 30 min, rather than 10 min, gave better results and yielded the corresponding products 8 in moderate to high isolated yields, whereas prolonged reaction times lowered the yields. After activation of 8 through prestirring in the presence of BF3•OEt2, the subsequent coupling with boronic acids 4 could be achieved at -78 °C to rt within 1-2 h even with electron-deficient 4. We found this method to be useful for preparation of a range of iodonium salts bearing electron deficient aryls as well as heteroaryl groups. Since 3-OTf generally offer advantages over 3-BF4 both in the purification and in applications, an in situ anion exchange is often performed by addition of triflic acid after the coupling with 4. Overall, this method increased the product yield and reduced the reaction time significantly. It is worth noting that certain tetrafluoroborate salts are more challenging to isolate compared to their triflate analogues, as they may form sticky brown solids upon the first trituration in diethyl ether. Full precipitation and isolation as off-white solids is possible through stirring the products in Et2O overnight.