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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

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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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Abstract

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 S_NAr 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

URL: https://doi.org/10.1021/acs.orglett.1c03317

DOI: 10.1021/acs.orglett.1c03317

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