Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(i) salt.

Title Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(i) salt.
Authors D.S. Rao; T.R. Reddy; S. Kashyap
Journal Org Biomol Chem
DOI 10.1039/c7ob03076b
Abstract

An efficient and highly chemoselective iodination of alkynes using a sulfonium iodate(i) electrophilc reagent under metal-free conditions has been realized. The reactivity of sulfonium iodate(i) salt could be significantly diverse in the presence of water as the solvent, enabling the (E)-1,2-diiodoalkenes stereospecifically. This stereodivergent approach is amenable to a wide range of alkyne substrates and demonstrates a diverse functional group tolerance resulting in synthetically valuable 1-iodoalkyne and (E)-vicinal-diiodoalkenes in good to excellent yields (up to 99%) with 100% selectivity under ambient conditions.

Citation D.S. Rao; T.R. Reddy; S. Kashyap.Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(i) salt.. Org Biomol Chem. 2018;16(9):15081518. doi:10.1039/c7ob03076b

Related Elements

Iodine

See more Iodine products. Iodine (atomic symbol: I, atomic number: 53) is a Block P, Group 17, Period 5 element with an atomic radius of 126.90447. The number of electrons in each of Iodine's shells is 2, 8, 18, 18, 7 and its electron configuration is [Kr] 4d10 5s2 5p5. The iodine atom has a radius of 140 pm and a Van der Waals radius of 198 pm. In its elemental form, iodine has a lustrous metallic gray appearance as a solid and a violet appearance as a gas or liquid solution. Elemental IodineIodine forms compounds with many elements, but is less active than the other halogens. It dissolves readily in chloroform, carbon tetrachloride, or carbon disulfide. Iodine compounds are important in organic chemistry and very useful in the field of medicine. Iodine was discovered and first isolated by Bernard Courtois in 1811. The name Iodine is derived from the Greek word "iodes" meaning violet.

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