Iodination of Alkyl Aryl Ethers by Mercury(II) Oxide-Iodine Reagent in Dichloromethane

Total Syntheses of the Tylophora Alkaloids Cryptopleurine, (−)‐Antofine, (−)‐Tylophorine, and (−)‐Ficuseptine C

“…This building block was prepared by regioselective iodination of veratrole 35 [36] followed by bromination of the resulting product 36 under standard conditions (Scheme 11). Although this compound contained some dibromide contaminant that could not be separated at this stage, it was amenable to a subsequent Suzuki reaction with the commercial boronic acid 38 under the previously optimized conditions [11,20] to give analytically pure biaryl 39.…”

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique

“…They are also important and the most reactive intermediates for various cross-coupling reactions and especially useful for formation of carbon-carbon and carbon-heteroatom bonds [4]. Recently the reagents reported for iodination of arenes include, iodine-nitrogen dioxide [5], iodine F-TEDA-[1-chloromethyl-4-fluoro-1,4-diazoniabicyclo [2,2,2] octane-bis-(tetrafluoroborate)] [6], bis-N-iodosuccinimide [7], trichloroisocyanuric acid-I2-Wet SiO2 [8], mercury(II)-oxide-iodine [9], iodine-monochloride [10], bis(pyridine)iodonium(I), tetrafluoroborate CF3SO3H [11], NIS-CF3SO3H [12], iodine silver sulfate [13], iodine-mercury salts [14] and NaOCl-NaI [15]. However, most of these methods suffer from major drawbacks such as use of harsh conditions, toxic heavy-metal catalysts, non-slectivity and longer reaction times.…”

A mild and simple iodination of phenols with trichloroisocyanuric acid/ I2 /Wet SiO2 system

“…Generally, arenes are iodinated by iodine in the presence of a Lewis acid or an oxidizing agent. Direct iodination methods have been reported using various iodonium donating systems, such as NIS-CF 3 SO 3 H, 5 iodine-Ag 2 SO 4 , 6 iodine-HgO, 7 NIS, 8 iodinetetrabutylammonium peroxydisulfate, 9 n-BuLi-CF 3 CH 2 I, 10 ICl, 11 and triiodoisocyanuric acid. [12][13][14] However, most of these methods require toxic and costly reagents, high temperatures and long reaction times.…”