Barely bidentate: The adduct of dimethylamino naphthalene (proton sponge) and 9-BBN-NTf2 is activated by steric hinderance for intermolecular borylation (see scheme). A contrasting addition/elimination pathway is favored when using monodentate triethylamine which gives the first observable borenium salt (9-BBN-NEt3+ Tf2N−) lacking any n- or π-donor substitutents.
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Prokofjevs et al. (2011) studied this question.
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