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Synthesis and Reactivity of 3,5-Diiodo-BODIPYs via a Concerted, Double Aromatic Finkelstein Reaction

Lookup NU author(s): Dr Paul Waddell, Dr Michael HallORCiD, Dr Julian Knight



This is the authors' accepted manuscript of an article that has been published in its final definitive form by American Chemical Society, 2021.

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3,5-Diiodo-8-aryl-BODIPYs are prepared from the corresponding 3,5-dicholoro- and 3,5-dibromo- congeners via a double aromatic Finkelstein reaction with NaI in refluxing propionitrile, in yields from 51-100%. Rate enhancement is observed for 3,5-dibromo-BODIPYs (ArBr > ArCl) suggesting a concerted SNAr mechanism for this transformation. Thus formed 3,5-diiodo-BODIPYs are examined as coupling partners in Migita-Kosugi-Stille, Mizoroki-Heck, Sonogashira and Suzuki-Miyaura reactions, providing routes towards complex BODIPY architectures.

Publication metadata

Author(s): Frank F, Waddell PG, Hall MJ, Knight JG

Publication type: Article

Publication status: Published

Journal: Organic Letters

Year: 2021

Volume: 23

Issue: 21

Pages: 8595-8599

Print publication date: 05/11/2021

Online publication date: 11/10/2021

Acceptance date: 07/10/2021

Date deposited: 07/10/2021

ISSN (print): 1523-7060

ISSN (electronic): 1523-7052

Publisher: American Chemical Society


DOI: 10.1021/acs.orglett.1c03317


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