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 subst rates while anchored on solid supports. The tactics make use of orthogonal protecting groups capable of inhibiting the reaction of the untargeted phen ol. Suitable groups are of ether and silyl type. The methodology has been d emonstrated on a biomolecule such as dermorphin where the integrity of one of two phenol functions is crucial for its biological activity. (C) 1999 El sevier Science Ltd. All rights reserved.