Reactivity and synthetic utility of 1-(arenesulfonyloxy)benziodoxolones

The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones wer e studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones i odinated various aromatics to give iodoarenes in moderate to good yields. I n particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1-(arenesulfonyloxy) benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aroma tic rings. Furthermore, the 1-(p-toluenesulfonyloxy)benziodoxolone/iodine s ystem iodotosyloxylated alkynes in good yields. These reactions proceeded v ia the formation of arenesulfonyl hypoiodites.