4-Iodobenzaldehyde → 1-(4-Ferrocenylphenyl)-2-(4-formylphenyl)acetylene

Participants

Reaction Steps

Samples of 4 (500 mg, 1.75 mmol), 4-iodobenzaldehyde (406 mg, 1.75 mmol), CuI (18 mg, 94 μmol) and Pd(PPh3)2Cl2 (8 mg, 11 μmol) were placed in a Schlenk flask. The flask was evacuated for 3 min and then the flask was backflushed with argon for 3 min. The process of evacuation and flushing was repeated 3 times. At this point flow rate was increased and the threaded stopcock was removed. Deaerated THF (5 mL) and DIEA (5.0 mL) were added in succession to the flask by gas-tight syringe. The threaded stopcock was replaced, the argon flow rate was reduced and the flask was immersed in an oil bath thermostated at 40° C. The reaction was stopped after 40 h. The mixture was then evaporated and the resulting orange solid was chromatographed (silica, CH2Cl2/hexanes, 1:1). The second orange band comprising the title compound was collected (579 mg, 84.9%). mp 219-220° C.; 1H NMR δ 4.10 (s, 5H), 4.42 (s, 2H), 4.73 (s, 2H), 7.52 (s, 4H), 7.72, 7.92 (AA′BB′, 4H), 10.07 (s, 1H); 13C NMR δ 67.3, 70.3, 70.5, 84.6, 89.4, 94.8, 120.2, 126.6, 130.4, 130.6, 132.6, 132.7, 135.9, 141.6, 192.2; EI-MS obsd 390.0696 (M+), calcd exact mass 390.0707; Anal. Calcd for C25H18FeO: C, 76.94; H, 4.65. Found: C, 76.75; H, 4.68.

Provenance & Evidence