Rapid aerobic iodination of arenes mediated by hypervalent iodine in fluorinated solvents. Issue 7 (15th February 2017)

• Record Type: Journal Article
• Authors: Iskra, Jernej; Murphree, S. Shaun
• Is Part Of: Tetrahedron letters. Volume 58:Issue 7(2017)
• Page Start: 645
• Page End: 648
• Publication Date: 2017-02-15
• Subjects: Aromatic substitution -- Hypervalent compounds -- Iodination -- Fluorinated solvents; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.01.003
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Moderately electron-rich arenes are the most suitable substrates for iodination. A catalytic mechanism involving dichloroiodic acid is proposed. Competitive formation of nitroarenes is observed in highly electron-rich substrates. Abstract: Arenes are rapidly converted to the corresponding iodides by aerobic oxidative iodination at room temperature by treatment with iodine and catalytic quantities of nitrous acid in a fluorinated solvent. Dichloroiodic acid is proposed as the actual iodination reagent.