1,2,4,5-Tetraiodobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a degassed solution of 1,2,4,5-tetraiodobenzene (5.81 g, 0.01 mol) in DMF-Et3N (100 mL, 1:1) were added Pd(PPh3)2Cl2 (350 mg. 0.5 mmol), CuI (200 mg, 1.2 mmol), and 4-pentyn-1-ol (4.2 g, 0.05 mol) was added drop-wise. The mixture was stirred under N2 at room temperature for 24 h. The solution was poured into water (400 mL). The mixture was extracted with CH2Cl2 (3×200 mL). The combined organic phases were washed with 5% HCl and brine, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography using CH2Cl2-MeOH (10:1, v/v) as eluent to afford tetramer (3.34 g, 82%): 1H NMR (300 MHz, CD3Cl+CO3OD δ ppm), 7.30 (s, 2H), 3.72 (t, J=6.3 Hz, 8H), 2.52 (t, J=7.2 Hz, 8H), 1.80 (p, J=6.6 Hz, 8H) ppm. was added drop-wise The mixture was extracted with CH2Cl2 (3×200 mL) The combined organic phases were washed with 5% HCl and brine dried over Na2SO4 concentrated under vacuum The residue was purified by silica gel column chromatography v/v) as eluent to afford tetramer (3.34 g, 82%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a degassed solution of 1,2,4,5-tetraiodobenzene (5.81 g, 0.01 mol) in DMF-Et3N (100 mL, 1:1) were added Pd(PPh3)2Cl2 (350 mg. 0.5 mmol), CuI (200 mg, 1.2 mmol), and 4-pentyn-1-ol (4.2 g, 0.05 mol) was added drop-wise. The mixture was stirred under N2 at room temperature for 24 h. The solution was poured into water (400 mL). The mixture was extracted with CH2Cl2 (3×200 mL). The combined organic phases were washed with 5% HCl and brine, dried over Na2SO4, and concentrated under vacuum. The residue was purified by silica gel column chromatography using CH2Cl2-MeOH (10:1, v/v) as eluent to afford tetramer (3.34 g, 82%): 1H NMR (300 MHz, CD3Cl+CO3OD δ ppm), 7.30 (s, 2H), 3.72 (t, J=6.3 Hz, 8H), 2.52 (t, J=7.2 Hz, 8H), 1.80 (p, J=6.6 Hz, 8H) ppm. was added drop-wise The mixture was extracted with CH2Cl2 (3×200 mL) The combined organic phases were washed with 5% HCl and brine dried over Na2SO4 concentrated under vacuum The residue was purified by silica gel column chromatography v/v) as eluent to afford tetramer (3.34 g, 82%)