Visible-Light Enabled Late-Stage, Room-Temperature Aminocarbonylation of Aryl Iodides with Labeled Carbon Monoxide

Abstract

In recent years, coupling reactions mediated by visible light have been widely studied because such reactions can often be run at significantly lower temperatures. In this work, aryl iodides were coupled with amines at ambient temperature in the presence of stoichiometric amounts of carbon monoxide using visible-light irradiation and palladium catalysis. A wide range of aryl substrates, both electron-deficient and rich, as well as heterocycles, were carbonylated to provide the corresponding amides in moderate to good yields based on CO. In addition, the generality of the amine was investigated, and primary and secondary amines yielded the desired products in moderate to good yields. This methodology was also successfully applied to the synthesis of pharmaceuticals and the incorporation of a carbon-14 label into the carbonyl group, where the use of 9-methyl-fluorene-9-carbonyl chloride (COgen) as the carbon isotope-labeled CO source allowed easy translation between the unlabeled and the labeled transformations.