Scheme 1.

Synthesis of naphthalimide–ortho-/meta-carborane conjugates 8–11. Reagents and Conditions: (i) HCCSi(CH₃)₃, Pd(PPh₃)₄, CuI, DMF, TEA, 2 h, 65 °C; (ii) TFA, H₂O, THF, 8 h, room temperature (RT); (iii) 1-(3-azidopropyl)-1,2-dicarba-closo-dodecaborane (4), CuSO₄⋅5H₂O, sodium ascorbate, THF/H₂O, 4 h, 35 °C (for 6); 1-(3-azidopropyl)-1,7-dicarba-closo-dodecaborane (5), CuSO₄⋅5H₂O, sodium ascorbate, and THF/H₂O, 2 h, 35 °C (for 7); (iv) N,N-dimethylethylenediamine (for 8 and 10), N-(2-aminoethyl)pyrrolidine (for 9 and 11), EtOH, 1 h, 35 °C and then 1 h, 45 °C. The yields of the compounds are given in parentheses.