Abstract
The dispersion-corrected density functional theory (M06-2X) was adopted to investigate the kinetically driven Bingel–Hirsch and thermodynamically controlled Prato reactions on Sc2@C2v(4059)-C66 which possesses the unconventional unsaturated linear triquinanes (ULTs), respectively. The mechanism differences of these two reactions on Sc2@C66 could lead to their different functionalization performances. The investigations on Bingel–Hirsch addition suggest that this process prefers to occur on the C–C bond (9–8) next to other than those (such as 9–10) on the ULT moieties, resulting in a highly regioselective product. The most favorable addition site (atom C9) for the bromomalonate anion is the only one that connects two equivalent [5,5] C–C bonds (10–11 and 31–30) among all possible atoms. In addition, solvent effect for this reaction was evaluated, and the results suggest that ortho-dichlorobenzene (ODCB) is more feasible than toluene for Sc2@C66. However, the Prato reaction for this system turned out to show poor regioselectivity to the best reactive bond 10–11.
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