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Updated: May 19, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of Functionalized [5]-Cyclo-m-phenylenes Enabled by Controlled Multihalogenation Using a Carborane Catalyst
Kohtaro Sugimoto1, Koji Hirano1,2, Yuji Nishii1,2,3
1Department of Applied Chemistry, Graduate School of Engineering, The University of Osaka, Suita, Osaka 565-0871, Japan.
None:
We report the synthesis of functionalized [5]CMP derivatives with unconventional substitution patterns. Controlled multiple bromination using a Carborane-SMe catalyst afforded key intermediate 2 in near-quantitative yield, followed by cyanation and alkynylation to furnish coupling products. The methyl substituent of Me5-[5]CMP served as a versatile handle for downstream derivatization. After benzylic bromination, diverse functional groups were introduced via nucleophilic substitution. Overall demethylation was achieved through the decarboxylation of the corresponding carboxylic acid.
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