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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.
For re-use rights please refer to the publisher's terms and conditions.
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.
Author(s): Frank F, Waddell PG, Hall MJ, Knight JG
Publication type: Article
Publication status: Published
Journal: Organic Letters
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
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