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Updated: Jan 17, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Anionic Iminoborane as Boryl Anion Synthon
Yuyang Dai1, Ping Cui1, Chen-Ho Tung1
1School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, China.
Abstract:
Classical iminoboranes, extensively investigated since the 1980s, are defined by 1,2-dipolar reactivity in which the boron center remains exclusively electrophilic. Here, we report an anionic iminoborane, [Ar─B≡N─Flu]-, in which substitution at nitrogen with a fluorenyl anion generates a conjugative B≡N─C: unit that enables cooperative reactivity. This species functions as a nucleophilic boryl anion synthon, engaging N-, P-, Se-, and Au-based electrophiles through a stepwise pathway initiated by carbanion attack followed by 1,3-migration to boron. In parallel, it acts as a BNC-1,3-dipole, undergoing [3 + n] cycloadditions with unsaturated substrates. These results demonstrate a rationally designed anionic iminoborane that provides a versatile platform for building diverse organoboron architectures beyond the classical chemistry of iminoboranes.
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