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Typical Experimental Procedure.
The alkene (0.1 mmol) was dissolved in MeOH (7 mL) and tetraethylammonium bromide (0.1 mmol), diselenide (0.01 mmol) and H2SO4 (1 µL) were added. The electrodes were inserted into the reaction mixture and constant current of 3 mA applied. After 6 h, electrolysis was stopped and the MeOH removed in vacuo. The mixture was dissolved in Et2O, washed with NaHCO3 solution and H2O before drying over MgSO4. The products were purified by preparative TLC or column chromatography.
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12 Spectroscopic data for 7a: 1H NMR (400 MHz, CDCl3): δ = 3.12 (s, 6 H), 3.65 (s, 3 H), 6.24 (d, J = 15.7 Hz, 1 H), 6.73 (d, J = 15.7 Hz, 1 H), 7.20-7.28 (m, 3 H), 7.38-7.40 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 49.7, 51.7, 100.9, 122.0, 126.9, 128.31, 128.33, 139.0, 147.8, 166.7 ppm. IR (NaCl): ν = 2950, 2832, 1727, 1659, 1449, 1436, 1304, 1276, 1192, 1167, 1072, 1046, 988, 700 cm-1. HRMS: m/z calcd for C13H16O4: 259.0941; found: 259.0941.
13 Spectroscopic data for 3d: 1H NMR (400 MHz, CDCl3): δ = 1.07 (d, J = 6.1 Hz, 3 H), 1.13 (d, J = 6.1 Hz, 3 H), 3.57 (sept, J = 6.1 Hz, 1 H), 3.64 (s, 3 H), 4.95 (dd, J = 5.4, 1.4 Hz, 1 H), 6.02 (dd, J = 15.6, 1.4 Hz, 1 H), 6.91 (dd, J = 15.6, 5.4 Hz, 1 H), 7.19-7.30 (m, 5 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 21.8, 22.6, 51.6, 69.5, 77.8, 120.1, 127.3, 128.0, 128.7, 140.0, 148.8, 166.9 ppm. IR (NaCl): ν = 2971, 1725, 1659, 1453, 1435, 1298, 1272, 1167, 1120, 978, 699 cm-1. HRMS: m/z calcd for C14H18O3: 252.1594; found: 252.1593.
14 Spectroscopic data for 3e: 1H NMR (400 MHz, CDCl3): δ = 2.06 (s, 3 H), 3.67 (s, 3 H), 5.97 (dd, J = 15.7, 1.5 Hz, 1 H), 6.32 (dd, J = 5.0, 1.5 Hz, 1 H), 6.95 (dd, J = 15.7, 5.0 Hz, 1 H), 7.27-7.31 (m, 5 H). 13C NMR (100 MHz, CDCl3): δ = 21.1, 51.8, 74.2, 121.2, 127.4, 128.83, 128.86, 137.1, 144.9, 166.4, 169.7. IR (NaCl): ν = 2952, 2918, 2849, 1738, 1727, 1662, 1436, 1372, 1310, 1279, 1228, 1197, 1171, 1069, 1022, 980, 699 cm-1. HRMS: m/z calcd for C13H14O4: 252.1230; found: 252.1229.
Diselenides 8 were synthesized according to literature procedures:
15a Compounds 8a,c: Wirth T.
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15b Compound 8b: Uehlin L.
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15c For compound 8d see ref. 5e.
16 Prepared by reaction of phenyl acetaldehyde and cyanoacetic acid. Spectroscopic data: Tsuji Y.
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18 Spectroscopic data for 7b: 1H NMR (400 MHz, CDCl3): δ = 3.11 (s, 6 H), 5.85 (d, J = 16.2 Hz, 1 H), 6.43 (d, J = 16.2 Hz, 1 H), 7.25-7.38 (m, 5 H) ppm. 13C NMR (100 MHz, CDCl3): δ = 49.8, 100.2, 101.4, 116.8, 126.9, 128.6, 128.8, 137.8, 154.0 ppm. IR (NaCl): ν = 2916, 2848, 2228, 1732, 1450, 1261, 1226, 1191, 1159, 1071, 1047, 972, 774, 746, 702 cm-1. HRMS: m/z calcd for C12H13NO2: 221.1285; found: 221.1283.
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