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Updated: Jun 5, 2025
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Boryl Radical Mediated Hydro(gem-diboryl)alkylation of Alkenes with Sterically Hindered NHC Boranes
Ruizeng Zhang1, Hao Zhang1, Pan Xu1
1College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.
Abstract:
NHC boryl radical mediated halogen atom transfer (XAT) is useful in organic synthesis. Yet, most of the reaction ends only with reducing the halogen to hydrogen, that is, the C-X to C-H. This is especially dominant for electron-deficient alkyl halides, where the formed electrophilic radical reacts rapidly with NHC boranes. Herein, by employing a sterically hindered NHC borane as the boryl radical precursor (IPr·BH3), we were able to use the electrophilic-deficient alkyl halide (α-Iodide gem-di(B(pin))methane) in the C-C bond formation reaction. Mono-, disubstituted styrene, aliphatic alkenes, and heteroatom-substituted alkenes were used as reaction partners. Forty hydro(gem-diboryl)methylation products were obtained at room temperature in moderate to good yields. Detailed mechanistic studies revealed that the reaction mainly involved the radical process.
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