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Updated: May 13, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Diastereoselective Synthesis of Boryl-Substituted Vinylcyclopropanes via Deborylative Cyclization of Geminal Diboron
Heng-Yu Gu1, Xin-Yi Chen1, Yi-Fei Yang1
1Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N Zhongshan Road, Shanghai 200062, China.
Abstract:
Herein we report a diastereoselective synthesis of boryl-substituted vinylcyclopropanes, a class of highly valuable synthetic building blocks, via deborylative cyclization of geminal diboron compounds. The method exhibits broad functional group tolerance and accommodates diverse alkyl and aryl α-substituents. The diastereoselectivity is primarily governed by the α-substituent (alkyl vs aryl), while olefin geometry in the side chain has a secondary influence. Mechanistic studies indicated distinct pathways: a concerted process for alkyl substrates and a carbanion intermediate for aryl derivatives. Synthetic utility of the products was also demonstrated.
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