Work

Investigation of boron–fluorine bond reactivity in meso -aryl-substituted BODIPYs towards carborane O -nucleophiles

Year: 2026

Type: article

Abstract: In this work meso -aryl-substituted BODIPYs (Ar = Ph, p -Br-C 6 H 4 , C 6 F 5 ) were used as starting compounds for modification of their boron atoms with carborane O -nucleophiles to afford novel boron-substituted carborane BODIPY derivatives. This type of reactions has not been used previously to prepare carborane structures. The reactions proceeded via the cleavage of boron–fluorine bonds in BODIPYs under the action of AlCl 3 followed by the treatment with carborane O -nucleophiles such as 1-hydroxymethyl- o -carborane or 1,2-dihydroxymethyl- o -carborane. While reactions of meso -aryl-substituted BODIPYs with 1-hydroxymethyl- o -carborane proceeded selectively, forming mono- or dicarborane-substituted BODIPYs, the reactions of 1,2-bis(hydroxymethyl)- o -carborane were not selective yielding a mixture of products. The structures of novel compounds were confirmed by 1 H and 11 B NMR and mass spectrometry. The structures of some prepared carborane BODIPY compounds were further supported by their single X-ray crystal structures.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.22.100

Authors: Andrei V Zaitsev, Alexander F Smol’yakov, Victoria M Alpatova, Elena G Kononova, Anatolii Botezatu, Valentina A Ol’shevskaya

Institutions: Russian Academy of Sciences, A. N. Nesmeyanov Institute of Organoelement Compounds

Language: English

Topic: Boron Compounds in Chemistry

Subfield: Radiology, Nuclear Medicine and Imaging

Field: Medicine

Domain: Health Sciences

Open Access status: diamond

Funder: Ministry of Science and Higher Education of the Russian Federation

Award: G41456476