Ligand-Enabled Copper-Mediated Radioiodination of Arenes

Org Lett. 2024 Feb 23;26(7):1528-1532. doi: 10.1021/acs.orglett.4c00356. Epub 2024 Feb 9.

Abstract

The discovery of a copper precatalyst that facilitates the key mechanistic steps of arene halodeboronation has allowed a step change in the synthesis of radioiodine-containing arenes. The active precatalyst [Cu(OAc)(phen)2]OAc was shown to perform room temperature radio-iododeboronation of aryl boronic acids with 1-2 mol % loadings and 10 min reaction times. These mild conditions enable particularly clean reactions, as demonstrated with the efficient preparation of the radiopharmaceutical and SPECT tracer, meta-iodobenzylguanidine (MIBG).