Binol → HCID 86706877, compound

Participants

Reaction Steps

The title compound was synthesized according to General Method D, utilizing 1,4-diiodobenzene (2.5 g, 7.6 mmol), 2-oxa-6-azaspiro[3.3]heptane oxalic acid salt (1.0 g, 6.9 mmol), CuI (0.26 g, 1.4 mmol), BINOL (0.40 g, 1.4 mmol), and K3PO4 (4.4 g, 21 mmol) in DMF (15 mL). The mixture was diluted with EtOAc, filtered through Celite and the filtrate was concentrated. Purification by flash chromatography (Biotage Isolera, 100 g HP-SIL, 10-50% EtOAc in hexanes) gave the title compound as a yellow solid (0.78 g, 37%). 1H NMR (400 MHz, CDCl3) δ ppm 7.47 (d, J=8.8 Hz, 2H), 6.22 (d, J=8.8 Hz, 2H), 4.82 (s, 4H), 3.98 (s, 4H); MS ESI 301.9 [M+H]+, calcd for [C11H12INO+H]+ 302.0.

Provenance & Evidence