Dichloromethane → 21H,22H-Porphine

Participants

Reaction Steps

The general procedure was used to couple 5,15-dibromo-10,20-diphenylporphyrin (31.0 mg, 0.05 mmol) with (+)-dihydrocholesterol (77.8 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 17 h. The title compound was isolated by flash chromatography (silica gel, methylene chloride: hexanes (v/v)=8:2) as a purple solid (27.5 mg, 45%). 1H NMR (300 MHz, CDCl3): δ 9.43 (d, J=4.8 Hz, 4H), 8.78 (d, J=4.8 Hz, 4H), 8.18 (m, 4H), 7.74 (m, 6H), 4.95 (s, 2H), 0.62-2.3 (m, 92H), −2.59 (s, 2H). UV-vis (CH2Cl2, λmax, nm): 418, 520, 557, 602, 660. HRMS-MALDI ([M+H]+): calcd for C86H115N4O2, 1235.9015, found 1235.90110 with an isotope distribution pattern that is the same as calculated one.

Provenance & Evidence