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IBX: A Novel and Versatile Oxidant for Electrophilic Thiocyanation of Indoles, Pyrrole and Arylamines
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2008
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Ammonium ThiocyanateNatural Product SynthesisDirect ThiocyanationEngineeringHeterocyclicAryl ThiocyanatesOrganic ChemistrySynthetic ChemistryChemistryHeterocycle ChemistrySynthesis MethodPharmacologyElectrophilic ThiocyanationBiomolecular EngineeringVersatile Oxidant
The direct thiocyanation of indoles and pyrrole with ammonium thiocyanate has been achieved using o-iodoxybenzoic acid (IBX) under mild and neutral conditions to produce indol-3-yl and pyrrol-2-yl thiocyanates, respectively, in excellent yields and with high selectivity. This method is effective even with N-substituted arylamines for the preparation of aryl thiocyanates.