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

Autor:	Felicity J. Frank, Michael J. Hall, Julian G. Knight, Paul G. Waddell
Rok vydání:	2021
Předmět:	chemistry.chemical_compound chemistry Nucleophilic aromatic substitution Organic Chemistry Sonogashira coupling Reactivity (chemistry) Propionitrile Physical and Theoretical Chemistry BODIPY Finkelstein reaction Biochemistry Medicinal chemistry
Zdroj:	Organic Letters. 23:8595-8599
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c03317
Popis:	3,5-Diiodo-8-aryl-BODIPYs are prepared from the corresponding 3,5-dichloro- and 3,5-dibromo- congeners via a double aromatic Finkelstein reaction with NaI in refluxing propionitrile, in yields from 51 to 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 toward complex BODIPY architectures.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::40de767413addb7138308b3c210b83da https://doi.org/10.1021/acs.orglett.1c03317 Zobrazit plný text záznamu