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Updated: Oct 25, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
A General Route to Silacyclohexanones via Regioselective Copper-Catalyzed Borylative Cyclization
Chen-Li Jin1, Ting Wu1, Rong-Jun Shi1
1Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Zhejiang Key Laboratory of Organosilicon Material Technology, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou311121, P. R. China.
Abstract:
A copper-catalyzed regioselective borylative cyclization of chloromethyl butenylsilanes with bis(pinacolato)diboron has been reported. The reaction proceeds via an endo-selective cyclization to deliver 4-silacyclohexyl boronates, which undergo a two-step oxidation sequence to afford 4-silacyclohexanones. DFT calculations corroborate the observed selectivity, highlighting the conformational role of the silicon center in favoring the six-membered rings. This protocol features readily available starting materials, a broad substrate scope, good functional group tolerance, and gram-scale capability. The synthetic utility of the resulting silacyclohexanones is demonstrated through diverse transformations, including ketalization, allylation, Wittig olefination, and Baeyer-Villiger oxidation.
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