Issue 9, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Dec 2017
Accepted
31 Jan 2018
First published
31 Jan 2018

Org. Biomol. Chem., 2018,16, 1508-1518

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

D. S. Rao, T. R. Reddy and S. Kashyap, Org. Biomol. Chem., 2018, 16, 1508 DOI: 10.1039/C7OB03076B

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