Gold(I)-Mediated Radioiododecarboxylation of Arenes

Abstract

A novel radioiodination method is developed using carboxylic acids as radiolabeling precursors. This method involves decarboxylation and organogold­(I) intermediate formation, enabling efficient radioiodination of (hetero)­arenes and cinnamic and phenylpropiolic acids. Additionally, we demonstrated the prolonged stability of crude gold­(I) organometallic compounds, showcasing their enduring radiolabeling capabilities.

Ligand-Enabled Copper-Mediated Radioiodination of Arenes

“…These include the click-type reaction of azides and alkynes in the presence of [ 125 I]­iodide, a Sandmeyer radioiodination of diazonium salts, and the use of silver­(I)-based Lewis acids for the radioiodination of electron-rich arenes . Methods using transition metals have also been reported, such as a nickel-mediated radioiodination of aryl bromides, arene C–H radioiodination using palladium acetate, and radio-iododecarboxylation of aryl carboxylic acids using gold­(I) intermediates . The widespread availability of aryl boronic acids and esters has meant that these have also been investigated as precursors for transition-metal-mediated radioiodination methods .…”

“… 10 Methods using transition metals have also been reported, such as a nickel-mediated radioiodination of aryl bromides, 11 arene C–H radioiodination using palladium acetate, 12 and radio-iododecarboxylation of aryl carboxylic acids using gold(I) intermediates. 13 The widespread availability of aryl boronic acids and esters has meant that these have also been investigated as precursors for transition-metal-mediated radioiodination methods. 14 In particular, several copper-mediated radioiodination reactions of aryl boron compounds have been reported.…”