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The forgotten borole: synthesis, properties and reactivity of a 1-boraindene.

ABSTRACT: The chemistry of unsaturated boron heterocycles, including five-membered boroles, continues to attract substantial interest. Herein, we report the synthesis of 1,2,3-triphenyl-1-boraindene, a benzene-fused borole, and examine its Lewis acidic, electrophilic, and antiaromatic properties relative to non-fused and bis-benzannulated boroles (9-borafluorenes). Reactivity studies with organic azides reveal that the boraindene behaves similarly to other boroles, undergoing ring expansion to a BN-naphthalene through insertion of a nitrogen atom.

SUBMITTER: Wieprecht N

PROVIDER: S-EPMC11304793 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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The forgotten borole: synthesis, properties and reactivity of a 1-boraindene.

Wieprecht Nele N Krummenacher Ivo I Wüst Leonie L Michel Maximilian M Fuchs Sonja S Nees Samuel S Härterich Marcel M Braunschweig Holger H

Chemical science 20240708 31

The chemistry of unsaturated boron heterocycles, including five-membered boroles, continues to attract substantial interest. Herein, we report the synthesis of 1,2,3-triphenyl-1-boraindene, a benzene-fused borole, and examine its Lewis acidic, electrophilic, and antiaromatic properties relative to non-fused and bis-benzannulated boroles (9-borafluorenes). Reactivity studies with organic azides reveal that the boraindene behaves similarly to other boroles, undergoing ring expansion to a BN-naphth ...[more]

PMID: 39118599

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