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

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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.

Graphical abstract: Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(i) salt

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Publication details

The article was received on 12 Dec 2017, accepted on 31 Jan 2018 and first published on 31 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03076B
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Chemoselective and stereospecific iodination of alkynes using sulfonium iodate(I) salt

    D. S. Rao, T. R. Reddy and S. Kashyap, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB03076B

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