Regioselective iodination of phenol and analogues using N-iodosuccinimide and p-toluenesulfonic acid

Targeting telomerase with radiolabeled inhibitors

“…Treatment of the diketone in acid affords the protected flavone and demethylation achieved using 1 M boron tribromide in dichloromethane at 0 °C yields the flavone product. In the case of 3 , iodinated hydroxyacetophenone 3a was prepared by reaction of 2,3-dimethoxy-2-hydroxyacetophenone with N -iodosuccinimide and p -toluenesulphonic acid in acetonitrile [59].…”

Total synthesis of illicidione A and illihendione A

“…18 Compound 15 was protected with two benzyl groups and was coupled with allylpinacol borane via the SuzukieMiyaura 19 coupling method to yield 17, which was then selectively debenzylated using BCl 3 to yield phenol 13 (Scheme 5). 20 Inspired by the result of the base-promoted 5-exo-tet cyclization, 21 after completely removing the TBS group of 9 using TBAF, K 2 CO 3 was directly added to yield 18 in an efficient one-pot reaction.…”

Regioselective iodination of chlorinated aromatic compounds using silver salts

“…3,4 Iodination with I 2 in ethanol resulted in complete conversion of 1b within 16 hours and displayed ortho selectivity; however, the yield of the ortho iodinated product 2b was only 16% (entry 1–1). N -Iodosuccinimide (NIS)/ p -toluenesulfonic acid (PTSA) as the iodine atom donating reagent 17 resulted in almost complete conversion of 1b within 24 h, with a 3b: 2b ratio of approximately 3: 1 (entry 1–2). A more pronounced regioselectivity has been reported previously for the iodination of phenol ( 1a ) with NIS/PTSA ( 3a: 2a > 14: 1).…”

“…A more pronounced regioselectivity has been reported previously for the iodination of phenol ( 1a ) with NIS/PTSA ( 3a: 2a > 14: 1). 17 …”

“…15,16 A variety of iodine atom donating reagents, such as N -iodosuccinimide/ p -toluenesulfonic acid 17 and iodine monochloride (ICl), 18 have been used successfully for the iodination of aromatic compounds. In addition, elemental iodine (I 2 ) is a particularly attractive source of iodine atoms.…”