Ligand-enabled copper-mediated radioiodination of arenes

McErlain, H., Andrews, M. J., Watson, A. J.B., Pimlott, S. L. and Sutherland, A. (2024) Ligand-enabled copper-mediated radioiodination of arenes. Organic Letters, 26(7), pp. 1528-1532. (doi: 10.1021/acs.orglett.4c00356) (PMID:38335124) (PMCID:PMC10897930)

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).

• Item Type: Articles
• Additional Information: Financial support from the Wellcome Trust (221295/Z/20/Z) and the University of Glasgow is gratefully acknowledged. We thank the EPSRC (EP/S027165/1) for funding. A.J.B.W. thanks the Leverhulme Trust for a Research Fellowship (RF-2022-014) and EPSRC Programme Grant “Boron: Beyond the Reagent” (EP/W007517/1) for support.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Pimlott, Dr Sally and Sutherland, Professor Andrew and Watson, Dr Allan and Mcerlain, Miss Holly
• Authors: McErlain, H., Andrews, M. J., Watson, A. J.B., Pimlott, S. L., and Sutherland, A.
• College/School: College of Medical Veterinary and Life Sciences > School of Medicine, Dentistry & Nursing; College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 09 February 2024
• Copyright Holders: Copyright © 2024 The Authors
• First Published: First published in Organic Letters 26(7):1528-1532
• Publisher Policy: Reproduced under a Creative Commons license