Compound 3b

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InChIKey YCGVNYUGIQQWMM-UHFFFAOYSA-N

Compound data: 1H NMR

Compound data: 13C{1H} NMR

Compound data: 19F NMR

Compound data: 1H-1H COSY

Compound data: HSQC

Compound data: HMBC

Compound data: Crystallographic data

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

Fe(OTf)₂ (0.013 g. 0.040 mmol), 2b (0.030 g, 0.077 mmol), NaO^tBu (0.007 g, 0.08 mmol) were combined in a 20 mL scintillation vial and dissolved in THF (10 mL). The purple solution was stirred under inert conditions for 72 h over which time the solution turned a deep green. The solvent was removed and the product was washed with pentane (3 x 10 mL), and extracted with THF. Isolated yield = 0.021 g (67 %). ¹H NMR (C₆D₆, 500 MHz, 25 °C): δ 8.96 (s, 2H, C₁₃-H), 8.52 (d, 2H, J_HH = 8.0 Hz, C₂₃-H), 8.44 (s, 2H, C₁-H), 7.97 (dd, 2H, J_HH = 5.0, 1.4 Hz, C₁₅-H), 7.81 (s, 2H, C₁₁-H), 7.54 (d, 2H, J_HH = 8.3 Hz, C₃-H), 7.41 (t, 2H, J_HH = 8.0 Hz, C₂₂-H), 6.92 (m, 2H, C₁₇-H), 6.82 (t, 2H, J_HH = 7.4 Hz C₄-H), 6.76 (d, 2H, J_HH = 8.0 Hz, C₂₁-H), 6.57 (t, 2H, J_HH = 7.5 Hz C₅-H), 6.40 (d, 2H, J_HH = 8.1 Hz, C₆-H), 5.90 ppm (dd, 2H, J_HH = 8.2, 5.0 Hz, C₁₆-H). ¹³C {¹H} NMR (C₆D₆, 125 MHz): 154.4 (C₁), 153.7 (C₁₄), 152.3 (C₂₀), 151.9 (C₁₉), 150.4 (C₁₅), 147.3 (C₁₀), 133.1 (C₁₇), 131.2 (C₇), 131.0 (C₁₈), 129.8 (C₄), 128.9 (C₂₂), 126.7 (C₆), 126.4 (C_{2, 8, 9, or 12}), 125.7 (C_{2, 8, 9, or 12}), 122.4 (C₃), 121.8 (C₁₆), 114.7 (C₂₁), 114.0 (C₂₃), 108.7 (C₁₃), 105.6 ppm (C₁₁); note: 3 peaks are missing due to solvent overlap (C_{2, 5, 8, 9, or 12}). ¹⁹F {¹H} NMR (CDCl₃, 470 MHz, 25 °C): δ -61.3 ppm. UV-Vis (CH₃CN): λ (ε) 259 (74 180), 319 (sh), 448 (29 300), 596 nm (17 800), 728 (9 370 M^-1 cm^-1). Anal. Calcd for FeC₄₆H₂₆N₆F₆: C, 66.36; H, 3.15. Found: C, 66.25; H, 3.32.