Unlocking Heteroaromatic Ring Systems through Chalcogen Insertion into Boroles

In this work, we report the reactivity of various annulated borole derivatives toward chalcogen (O, S, and Se) insertion. Among a series of 9-borafluorenes with different boron substituents (Ph, Br, or o-carboranyl) and a mixed thiophene-benzene-fused derivative, only the 9-o-carboranyl-substituted...

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Bibliographic Details
Published in:Inorganic chemistry 2023-12, Vol.62 (51), p.21329-21335
Main Authors: Bischof, Tobias, Wieprecht, Nele, Fuchs, Sonja, Endres, Lukas, Krummenacher, Ivo, Michel, Maximilian, Mihm, Cornelius, Braunschweig, Holger, Finze, Maik
Format: Article
Language:English
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Summary:In this work, we report the reactivity of various annulated borole derivatives toward chalcogen (O, S, and Se) insertion. Among a series of 9-borafluorenes with different boron substituents (Ph, Br, or o-carboranyl) and a mixed thiophene-benzene-fused derivative, only the 9-o-carboranyl-substituted 9-borafluorene yielded the complete set of chalcogen-containing heteroarenes, including the first 1,2-selenaborinine derivative. To evaluate the aromaticity of this heterocyclic analogue of phenanthrene, nucleus-independent chemical shift (NICS) values were computed and compared to those of its lighter group 16 congeners.
ISSN:0020-1669
1520-510X
DOI:10.1021/acs.inorgchem.3c03403