Reaction Steps
The general procedure was used to couple 5-bromo-10,20-diphenylporphin (27.1 mg, 0.05 mmol) with estrone (27 mg, 0.1 mmol), using Pd2(dba)3 (2.3 mg, 0.0025 mmol) and DPEphos (5.38 mg, 0.01 mmol) in the presence of Cs2CO3 (37.6 mg, 0.1 mmol). The reaction was conducted in THF at 100° C. for 24 h. The title compound was isolated by flash chromatography (silica gel, methylene chloride: hexanes (v/v)=8:2) as a purple-red solid (20 mg, 55%). 1H NMR (300 MHz, CDCl3) δ 10.13 (s, 1H), 9.39 (d, J=4.8 Hz, 2H), 9.29 (d, J=4.8 Hz, 4H), 8.98 (d, J=4.8 Hz, 4H), 8.86 (d, J=4.8 Hz, 4H), 8.22 (m, 4H), 7.75 (m, 6H), 7.14 (d, J=9.0 Hz, 1H), 6.88 (d, J=8.4 Hz, 1H), 6.64 (d, J=1.8 Hz, 1H), 1.86-2.62 (m, H from estrone), 1.26-1.52 (m, H from estrone), 0.85 (s, 3H), −2.77 (s, 2H). 13C NMR (75 MHz, CDCl3): δ 141.2, 138.1, 134.7, 133.0, 131.5, 130.8, 127.9, 127.8, 126.9, 126.5, 120.2, 119.7, 116.6, 114.1, 104.6, 50.3, 47.9, 44.0, 38.1, 35.8, 31.5, 29.4, 26.3, 25.8, 21.5, 13.8. UV-vis (CH2Cl2, Amax, nm): 413, 510, 544, 585, 641. HRMS-EI ([M]+): calcd for C50H42N4O2, 730.3308, found 730.3294.
