chemoselective-preparation-1-iodoalkynes-12-diiodoalkenes-112

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

We present the chemoselective synthesis of 1-(iodoethynyl)-4-methylbenzene, 1-(1,2-diiodovinyl)-4-methylbenzene, and ...

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.

Hypervalent Iodine Mediated Chemoselective Iodination of Alkynes.

The uncontrolled redox activity of metal ions, especially copper, in the brains of patients with Alzheimer's disease (AD) should be considered the origin of intense oxidative damage to neurons in the AD brain. To obtain low-molecular-weight copper chelators that act as tetradentate ligands, we designed new compounds based on an 8-aminoquinoline motif with a lateral chain attached at the 2-position of the aromatic ring. Some of these new ligands, termed TDMQ for TetraDentate MonoQuinolines, are specific for copper chelation. Full characterization of these ligands is reported, as well as their affinities for Cu , and their capacities to inhibit oxidative stress induced by copper-amyloids activated by a reductant. Such metal ligands can be considered as potential anti-AD agents, as they should be able to regulate the homeostasis of copper in brain tissue.

Article	Year
Hypervalent Iodine Mediated Chemoselective Iodination of Alkynes. The Journal of organic chemistry\| PubMed ID: 28803465	2017
Preparation of Tetradentate Copper Chelators as Potential Anti-Alzheimer Agents. ChemMedChem\| PubMed ID: 29420864	2018

Ju Huang

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