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Improved aromatic Finkelstein reactions for the synthesis of iodinated BODIPYs

Lookup NU author(s): Marissa Nalenan, Dr Paul Waddell, Dr Michael HallORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

Iodinated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) are valuable synthetic intermediates for the formation of functionalised fluorophores, as they enable downstream nucleophilic aromatic substitution (S_NAr) and metal-catalysed cross-coupling reactions. However, there are limited synthetic routes available for the synthesis of such iodinated BODIPYs, particularly for the selective introduction of iodine at the 1, 3, 5 and 7-positions. Herein, we present an improved route to iodinated BODIPYs, based on an aromatic Finkelstein reaction, in which bromo-substituted BODIPYs are transformed into their corresponding iodo-analogues. Our optimised reaction conditions, excess NaI in refluxing acetone for 1.5 hours, allowed for the formation of 3,5-diiodo-8-aryl-BODIPYs in high yields (90-95%). Furthermore, the aromatic Finkelstein reactions of bromo-substituted BODIPYs with NaI show high regioselectivity for the 1, 3, 5 and 7-positions, with the 2, 6-positions being unreactive. This allows for the efficient formation of mixed bromo/iodo-substituted BODIPYs, through the preferential substitution of bromines at the 1, 3, 5 and 7-positions. We anticipate that this high yielding and highly regioselective pathway for the synthesis of iodo-BODIPYs will be impactful in the further development of functionalised BODIPY platforms.

Publication metadata

Author(s): Nalenan MYA, Waddell PG, Hall MJ

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2026

Volume: 24

Issue: 33

Pages: 6826-6832

Print publication date: 24/08/2026

Online publication date: 04/08/2026

Acceptance date: 04/08/2026

Date deposited: 05/08/2026

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/D6OB01090C

DOI: 10.1039/D6OB01090C

Data Access Statement: The data supporting this article have been included as part of the Supplementary Information. CCDC 2466462-2466472 and 2523513-2523514 contain the supplementary crystallographic data for this paper.

Notes: preprint https://doi.org/10.26434/chemrxiv.15006216/v1

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