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

Nele WieprechtIvo KrummenacherLeonie WüstMaximilian MichelSonja FuchsSamuel NeesMarcel HärterichHolger Braunschweig
Published in: Chemical science (2024)
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.
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