[Hydroxy(tosyloxy)iodo]benzene

Pale yellow crystalline powder

Versatile synthetic reagent in phenyliodination and/or tosylation of a range of organic substrates; in oxidative transformations including oxidative rearrangements.

Reactant for:

• Ligand-free palladium-catalyzed Heck-type coupling reactions
• Preparation of carbodiimides via dehydrosulfurization of thioureas
• Preparation of nitriles by oxidative conversion of alcohols, aldehydes, and amines
• Preparation of substituted anilines via aromatic aldoxime reaction
• Preparation of tetrahydrofurans by oxidative cyclization of homoallylic alcohols
• Preparation of isoxazoline N-Oxides from -hydroxyketoximes via oxidative N-O coupling
• Ring expansion in synthesis of aminopeptidase inhibitors
• Oxidation and protonation reactions in acidic conditions

reagent type: oxidant

Possible impurities are tosic acid (removed by washing with Me2CO) and acetic acid (removed by washing with Et2O). It is purified by dissolving in the minimum volume of MeOH, adding Et2O to cloud point and setting aside for the prisms to separate [Koser & Wettach J Org Chem 42 1476 1977, NMR: Koser et al. J Org Chem 41 3609 1976]. It has also been crystallised from CH2Cl2 (needles, m 140-142o) [Neiland & Karele J Org Chem, USSR (Engl Transl) 6 889 1970].