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Updated: Jan 8, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

トリス（カルボラニル）ボラン環境を有するルイス超酸性ボラン誘導体の合成

Libo Xiang¹, Junyi Wang², Alexander Matler¹

¹Institute for Inorganic Chemistry and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Würzburg 97074, Germany.

Inorganic chemistry

|December 12, 2025

Abstract:

The title compound, a carborane-fused borirane bearing an additional iPr-substituted carboranyl group (C₂B₁₀H₁₀)B(C₂B₁₀H₁₀iPr), was successfully synthesized via salt elimination between [Li₂C₂B₁₀H₁₀] and (C₂B₁₀H₁₀iPr)BBr₂, and fully characterized in both the solid state and in solution. Benefiting from the unique tris(carboranyl)borane environment, the Lewis acidity of the boron center in this borirane is significantly enhanced compared to conventional boriranes. Its fluoride ion affinity (FIA) is greater than that of SbF₅, allowing it to be classified as a Lewis superacid for the first time among boriranes. In addition, the compound stores a substantial amount of ring strain energy within its carborane-fused three-membered ring. The combination of Lewis superacidity and ring strain gives rise to unprecedented reactivity patterns, including (1) an NHC-triggered intramolecular transfer hydrogenation in which an alkane moiety serves as the hydrogen source; (2) a formal CB/CO σ-bond metathesis reaction with THF, representing a new mode of THF ring-opening; and (3) a dearomative N-C bond insertion reaction with DMAP.

キーワード:

ボランカルボランルイス超酸有機ホウ素化学環ひずみ

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

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