A mild method for introducing iodine monofluoride into alkenes and iodination of aromatics using xenon difluoride

Electrophilic Iodination of Organic Compounds Using Elemental Iodine or Iodides

“…Benzene and naphthalene were directly iodinated to iodobenzene (2) or 1-iodonaphthalene (4) using several iodinating systems (Table 1). Transformations using iodine and the oxidants chromium(VI) oxide, 18 sodium percarbonate (SPC) 19 or iodopentoxide 20 under anhydrous and strongly acidic conditions gave moderate to good yields of 2 (entries 1-3), while oxidative activation with polyvinylpyrrolidone-supported hydrogen peroxide (PVP-H 2 O 2 ) catalysed by tungstophosphoric acid, 21 the charcoal-supported complex Fe(NO 3 ) 3 •1.5N 2 O 4 , 22a xenon di- fluoride, 23 or with poly[styrene-(iodosodiacetate)] 27 could be performed under milder reaction conditions (entries 4, 5,8,11,16). Activation following iodide trapping by mercury(II) 24 or silver(I) 25 ions was also applied (entries 9, 10) and moderate to excellent yields obtained, while oxidative iodination by alkali metal iodides and potassium bromate under acidic conditions 22c (entries 7 and 13), concentrated sulfuric acid, 26 (entry 15), cerium(IV) trihydroxide hydroperoxide in aqueous sodium dodecyl sulfate (SDS), 22b (entries 6 and 12) or polymer-supported hydrogen peroxide 21 (entries 4 and 14) were also used for this derivatisation of benzene or naphthalene.…”

Functionalization of Alkynes for Preparing Alkenyl Fluorides

“…Shellhamer and coworkers found that iodine monofluoride (IF) could be generated from XeF 2 and I 2 , thus giving access to fluoroiodohexene 84 under mild conditions (Fig. 33) [53]. A more general approach for halofluorination of alkynes was achieved by Olah's group (Fig.…”

Chemistry of xenon derivatives. Synthesis and chemical properties

“…218 A method for iodination of aromatic compounds by a mixture of XeF 2 with iodine or N-iodosuccinimide has recently been described. 172,220 It is noteworthy that the same mixture was used for iodofluorination of alkenes. The IF generated from xenon difluoride is less reactive than that synthesised from I 2 and F 2 .…”