Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Hypervalent Iodine Mediated Chemoselective Iodination of Alkynes

Hypervalent Iodine Mediated Chemoselective Iodination of Alkynes
Yan Liu, Ju Huang, Keiji Maruoka, Daya Huang
Reported herein are practical approaches for the chemoselective mono-, di-, and tri-iodination of alkynes based on efficient oxidative iodinations catalyzed by hypervalent iodine reagents. The reaction conditions were systematically optimized by altering the iodine source and/or the hypervalent iodine reagent system. The tetrabutylammonium iodide (TBAI)/(diacetoxyiodo)benzene (PIDA) system is specific for monoiodination, while the KI/PIDA system results in di-iodination. Combining the TBAI/PIDA and KI/PIDA systems in one pot provided the corresponding tri-iodination products efficiently. These reaction conditions can be applied to the synthetically important iodination of aromatic and aliphatic alkynes, which was accomplished in good yield (up to 99%) and excellent chemoselectivity. These synthetic methods can also be applied to the efficient chemoselective synthesis of iodoalkyne derivatives, intermediates, and related biologically active compounds.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01555

DOI: 10.1021/acs.joc.7b01555

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