Facile Synthesis of E‐Diiodoalkenes: H₂O₂‐Activated Reaction of Alkynes with Iodine

Abstract

Hydrogen peroxide was found to activate iodine in the addition reaction with triple bonds. A facile and technologically straightforward procedure was developed for the synthesis of E‐diiodoalkenes based on the reaction of alkynes with an I₂–H₂O₂ system in THF. Selective iodination of terminal and internal alkynes containing electron‐donating and electron‐withdrawing substituents afforded 16 E‐diiodoalkenes in yields up to 89%.

Keywords:

• alkynes
• E‐diiodoalkenes
• hydrogen peroxide
• iodination

Acknowledgments

This work is supported by the Program for Support of Leading Scientific Schools of the Russian Federation (Grant NSh 5022.2006.3), the Grant of President of Russian Federation (No. MK‐3515. 2007. 3), the Russian Foundation for Basic Research (Grant No. 07‐03‐00338), and the Russian Science Support Foundation.