Abstract
Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: recyclable hypervalent iodine reagents
Highlights
Organohypervalent iodine compounds are widely used in organic synthesis as versatile and environmentally friendly reagents for various oxidative transformations.[1,2,3,4,5,6,7]
Our group reported the preparation of pyridine-based pentavalent iodine reagents, 2-iodylpyridines, by oxidation of corresponding 2-iodopyridines using 3,3-dimethyldioxirane
We have found that the reaction of 2-iodopyridine 6 with the HCl-NaOCl combination for 2 hours at room temperature yields 2-(dichloroiodo)pyridine 7 in 89% yield (Scheme 2, eq 1)
Summary
Organohypervalent iodine compounds are widely used in organic synthesis as versatile and environmentally friendly reagents for various oxidative transformations.[1,2,3,4,5,6,7] In particular, (dichloroiodo)arenes, ArICl2, are commonly applied as efficient oxidants or chlorinating reagents.[8] (Dichloroiodo)benzene 1 is one of the most common reagents that can be conveniently prepared by direct chlorination of iodobenzene.[9]. Chlorination of 2-iodopyridine 6 (410 mg, 2.00 mmol) according to the general procedure afforded 490 mg (89%) of product 7, isolated as a yellow solid: mp 79.5-81.1 oC (from methylene chloride); IR (KBr) cm-1 3077, 1556, 1444, 1412; 1H NMR (500 MHz, CDCl3): δ 8.53 (dd, J 4.9 Hz, 1.8 Hz, 1H), 8.19 (dd, J 8.3 Hz, 0.5 Hz, 1H), 7.84 (ddd, J 8.3 Hz, 7.4 Hz, 1.8 Hz, 1H), 7.59 (ddd, J 7.4 Hz, 4.9 Hz, 0.5 Hz, 1H); 13C
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