Sodium Iodide → HCID 46830733, compound

Participants

Reaction Conditions

Reaction Steps

(Bowden, et al., Tetrahedron 2000, 56, 3393-3408) Diazonium salt 1 (11.7 mg, 0.0368 mmol) was added to a mixture of phenylacetylene (11.4 mg, 0.0805 mmol), sodium iodide (9.8 mg, 0.065 mmol), and Pd(OAc)2 (0.5 mg, 0.002 mmol) in 0.23 g of 95% ethanol. Then triethylamine (10.6 mg, 0.077 mmol) was added to the mixture. The reaction mixture was stirred at 70° C. for 22 h, then filtered through a pad of SiO2 with the help of hexane. Removal of the solvent gave a pale yellow crystalline solid which were purified by SiO2 column chromatography with hexane to give 24a as a colorless oil (1.0 mg; 9%); m.p. 88.0-89.0° C. IR (ATR): {tilde over (v)}=2926, 2222, 1603, 1503, 1445, 1402, 1094, 835 cm−1. MS (GC, EI): m/z=304 [M+], 196. 1H NMR (500 MHz, CDCl3): δ=7.74 (d, J=9.0 Hz, 2H), 7.60 (d, J=9.0 Hz, 2H), 7.55 (m, 2H), 7.39-7.37 (m, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=153.0 (C), 131.8 (2CH), 131.6 (2CH), 129.0 (CH), 128.5 (2CH), 127.0 (C), 126.0 (2CH), 122.2 (C), 92.2 (C), 87.2 (C) ppm. 19F NMR (470 MHz, CDCl3): δ=84.0 (quint, J=150 Hz, 1 F), 62.7 (d, J=150 Hz, 4 F) ppm.

Provenance & Evidence