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Updated: Feb 22, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Merging [2+2] Cycloaddition with Radical 1,4-Addition: Metal-Free Access to Functionalized
Feng Liu1, Jia-Yin Wang1, Peng Zhou2
1School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu, 221116, China.
Abstract:
A metal-free [2+2] cycloaddition and 1,4-addition sequence induced by S-centered radicals has been achieved by treating benzene-linked allene-ynes with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) in a one-pot procedure. The reaction provides a greener and more practical access to functionalized cyclobuta[a]naphthalen-4-ols with valuable applications. More than 50 examples are demonstrated with excellent diastereoselectivity and chemical yields. The reaction pathway is proposed to proceed by the following steps:[2+2] cycloaddition, insertion of SO2 , 1,4-addition, diazotization, and tautomerization.
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