Compound 3k

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Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

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

General procedure B: A sealed tube with magnetic stir bar was charged with Pd(OAc)2 (10 mol%, 2.2 mg), [F⁺]PF₆^- (0.15 mmol, 42.7 mg), C₆F₅CO₂H (0.5 mmol, 106.0 mg), substrate (0.1 mmol), and TDG4 (25 mol%, 4.6 mg) in air. Then, DCM-d2 (0.45 mL) was added as solvent. The reaction mixture was stirred at room temperature for 1 h, then at 70 ^oC for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, and the yields of the fluorination products were directly determined by ¹H NMR analysis of the crude product using CH₂Br₂ (0.2 mmol, 14 uL) as the internal standard.1k was fluorinated following general procedure B described above (58% NMR yield of 3k). ¹H NMR (600 MHz, CDCl₃): δ 10.49 (s, 1H), 7.64 (td, J = 8.1, 5.7 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.15 (ddd, J = 10.7, 8.3, 1.0 Hz, 1H), 6.39 (dq, J = 48.7, 6.2 Hz, 1H), 1.60 (dd, J = 24.3, 6.2 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 188.52 (d, J = 11.8 Hz), 165.94 (dd, J = 258.0, 1.9 Hz), 146.59 (d, J = 20.0 Hz), 136.19 (dd, J = 10.3, 1.4 Hz), 120.96 (dd, J = 15.0, 3.6 Hz), 120.04 (dd, J = 6.3, 4.2 Hz), 115.38 (d, J = 21.4 Hz), 87.97 (dd, J = 168.4, 2.7 Hz), 23.20 (d, J = 24.8 Hz). ¹⁹F NMR (376 MHz, CDCl₃): δ –121.00 (d, J = 4.9 Hz), –173.57 (d, J = 4.8 Hz). HRMS (ESI-TOF): m/z calculated for C₉H₉F₂O⁺ [M+H]⁺ 171.0616, found 171.0620.