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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Copper-catalyzed stereospecific methoxyboration of styrenes enabled by oxygen umpolung with acetal-based peroxides
Kyosuke Fujiwara1, Shogo Nakamura1, Koji Hirano1,2
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University Suita Osaka 565-0871 Japan k_hirano@chem.eng.osaka-u.ac.jp.
Abstract:
An oxygen-umpolung-enabled, regioselective and stereospecific copper-catalyzed methoxyboration of styrenes with diborons and acetal-based methyl peroxide has been developed. The use of designed peroxide enables the otherwise difficult two-electron redox event under the borylcopper catalysis, thus delivering the corresponding oxyborated products with high stereospecificity. Combined with the stereospecific post functionalizations of the boron moiety, the copper catalysis can provide facile access to the stereochemically defined, functionality-rich alkyl ether derivatives ubiquitously found in bioactive molecules and functional materials.
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