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. 2018 Mar 19;9(15):3881–3891. doi: 10.1039/c8sc00743h

Scheme 1. The members of the triad 1H2/Li[1H]/Li2[1] are linked through redox processes as well as protonation/deprotonation reactions. Treatment of 1H2 with RCH2Li leads to C(sp3)–H activations and skeletal rearrangements to furnish 1,1-bis(9-borafluorenyl)methanes (together with Li[1H]; R = H, C3H7). The addition of haloalkanes RX to Li2[1] results in nucleophilic substitution reactions and again skeletal rearrangements to afford 9-R-9-borafluorenes (in some cases accompanied by C(sp3)–H activations; X = Cl, Br, I). Carbon atoms marked with asterisks bear tBu substituents.

Scheme 1