Synthesis of Imidazole Adducts of BH3, BF3, and B3H7 and Comparison of Their Nucleophilic Substitution Reaction Activity
Jia-Rui Chang , Lei Cao , Sihan Jia , Fei Fang , Zi-Heng Fan , Qiao-Jing Pan , Yan-Na Ma , Xuenian Chen
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (8) : 925 -930.
Synthesis of Imidazole Adducts of BH3, BF3, and B3H7 and Comparison of Their Nucleophilic Substitution Reaction Activity
N-Methylimidazole borane adducts were synthesized and their reactivities with different electrophiles after deprotonation were compared. Subsequently, we used the more stable and reactive imidazole adducts with B3H7, a multinuclear borane, to generate various C2, C2 benzyl, and C2,5-disubstituted imidazole adducts of B3H7 under mild reaction conditions. Some 2,5-disubstituted imidazole products are usually difficult to synthesize directly from imidazole molecules. Furthermore, the borane moiety of these adducts can be easily removed to obtain the corresponding imidazoles. The higher reactivity of the imidazole adducts of B3H7 compared to their corresponding imidazoles may be attributed to the σ-aromaticity of B3H7 or mediated by double hydrogen bonds.
Borane adducts / Nucleophilic substitution / Imidazole compounds / Organoboron compounds / Boranes / Lewis acids / N-Heterocycles / Triborane
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.
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