Compound 7

1,1,3,3-tetrakis(3,3'',5,5''-tetrakis(trifluoromethyl)-[1,1':3',1''-terphenyl]-5'-yl)isoindoline-2-carboselenaldehyde

From: A crystalline monosubstituted carbene

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Compound data: 77Se NMR

Compound data: Crystallographic data

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

In a 15-mL scintillation vial, a mixture of 2c (47.3 mg, 20 µmol), elemental selenium (5.0 mg, 63 µmol), and KHMDS (6.0 mg, 30 µmol) was chilled for 1 hour in a glovebox coldwell cooled with dry ice/acetone bath. Then, pre-cooled THF (2.0 mL) was added, and the mixture was stirred with cooling for 30 minutes. The cooling bath was removed, and the mixture was stirred at room temperature overnight. The resulting mixture was passed through a glass filter, and the filtrate was evaporated to dryness. The solid residue was recrystallized from chloroform/hexane (vapour diffusion) at room temperature, giving 7 as orange crystals suitable for X-ray crystallographic analysis. The crystals were grounded and dried in vacuo at 120 °C overnight, to afford 7 as an orange powder (28.7 mg, 13 µmol, 65% yield). NOTE: Compound 7 is mildly sensitive to water, decomposing to formamide. 1H NMR (300 MHz, CDCl3) δ 11.99 (s, 1H, NCHSe), 7.84–7.78 (m, 10H), 7.73 (m, 4H), 7.69 (br s, 16H), 7.63–7.58 (m, 5H), 7.51 (m, 4H), 7.38 (d, J = 7.0 Hz, 1H); 13C NMR (126 MHz, CDCl3) δ 192.4 (1C, NCHSe), 144.5 (2C, 4°), 143.3 (1C, 4°), 141.5 (4C, 4°), 140.8 (4C, 4°), 140.6 (4C, 4°), 140.0 (1C, 4°), 139.3 (2C, 4°), 139.0 (4C, 4°), 132.6 (q, J = 33.6 Hz, 8C, 4°), 132.3 (q, J = 33.6 Hz, 8C, 4°), 131.3 (1C, 3°), 130.9 (1C, 3°), 129.3 (4C, 3°), 127.6 (4C, 3°), 126.8 (20C, 3°), 125.7 (1C, 3°), 124.9 (1C, 3°), 122.9 (q, J = 275.6 Hz, 8C, 4°), 122.8 (q, J = 275.6 Hz, 8C, 4°), 122.3 (4C, 3°), 121.9 (4C, 3°), 86.7 (1C, 4°), 83.3 (1C, 4°); 19F NMR (282 MHz, CDCl3) δ −63.1, −63.2; 77Se NMR (57 MHz, CDCl3) δ 978.7 (Note: While acetone-d6 is a standard solvent for 77Se NMR study, Ulrich and coworkers reported that 77Se NMR signals observed in CDCl3 are in good agreement with those observed in acetone-d6.6); HRMS (m/z): [M+TFA−H] calcd. for C97H41F48NSe·CF3CO2, 2324.1514; found, 2324.1493.