Reaction Steps
The general procedure was used to couple 5,15-dibromo-10,20-diphenylporphyrin (31.0 mg, 0.05 mmol) with (+)-estrone (108 mg, 0.2 mmol), using Pd2(dba)3 (4.6 mg, 0.005 mmol) and DPEphos (10.7 mg, 0.02 mmol) in the presence of Cs2CO3 (65.2 mg, 0.2 mmol). The reaction was conducted in toluene at 100° C. for 40 h. The title compound was isolated by flash chromatography (silica gel, methylene choloride:ethyl acetate (v/v)=9:1) as a purple solid (49.1 mg, 98%). 1H NMR (300 MHz, CDCl3): δ 9.30 (d, J=4.5 Hz, 4H), 8.78 (d, J=4.8 Hz, 4H), 8.16 (m, 4H), 7.74 (m, 6H), 7.16 (d, J=8.4 Hz, 1H), 7.13 (d, J=8.4 Hz, 1H), 6.89 (d, J=8.4, 2.7 Hz, 1H), 6.86 (d, J=8.4, 3.0 Hz, 1H), 6.65 (d, J=3.0 Hz, 2H), 1.20-2.8 (m, 30H), 0.88 (s, 3H), 0.86 (s, 3H), −2.47 (s, 2H). 13C NMR (75 MHz, CDCl3): δ 141.1, 138.1, 134.6, 133.1, 132.0, 131.3, 131.0, 127.8, 126.9, 120.2, 116.3, 114.0, 50.3, 47.9, 44.0, 38.3, 38.1, 35.9, 31.5, 29.4, 26.3, 25.8, 21.5, 13.8. UV-vis (CH2Cl2, λmax, nm): 420, 517, 555, 598, 655. HRMS-EI ([M]+): calcd for C68H62N4O4, 998.4771, found 998.4773 with an isotope distribution pattern that is the same as calculated one.
