Selective solid-phase iodination of phenolic groups with bis(pyridine)iodonium (I) tetrafluoroborate

Selective direct aromatic electrophilic iodination of target phenol groups can be performed by the IPy2BF4 reagent on multiple phenol containing substrates while anchored on solid supports. The tactics make use of orthogonal protecting groups capable of inhibiting the reaction of the untargeted phenol. Suitable groups are of ether and silyl type. The methodology has been demonstrated on a biomolecule such as dermorphin where the integrity of one of two phenol functions is crucial for its biological activity. (C) 1999 Elsevier Science Ltd. All rights reserved.