Copper-Mediated Radiobromination of (Hetero)Aryl Boronic Pinacol Esters

2023/02/06 by Jason C. Mixdorf, Sabrina Hoffman, Sabrina L. V. Hoffman +5 · 8 citations
Chemistry · Medicine · #Alkyl #Aryl #Bromide #Cancer Treatment and Pharmacology #Catalysis #Chemistry #Combinatorial chemistry #Copper #Halogenation #Iodide #Medicinal chemistry #Organic chemistry #PARP inhibition in cancer therapy #Pinacol #Radiopharmaceutical Chemistry and Applications #Steric effects

paper · doi:10.1021/acs.joc.2c02420

openalex publication_date 2023/02/06 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/06

Abstract

A copper-mediated radiobromination of (hetero)aryl boronic pinacol esters is described. Cyclotron-produced [ 76/77 Br]bromide was isolated using an anion exchange cartridge, wherein the pre-equilibration and elution solutions played a critical role in downstream deboro-bromination. The bromination tolerates a broad range of functional groups, labeling molecules with ranging electronic and steric effects. Bologically active radiopharmaceuticals were synthesized, including two radiobrominated inhibitors of poly ADP ribose polymerase, a clinically relevant chemotherapeutic target for ovarian, breast, and prostate cancers.

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