Compound 106

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Compound data: NMR

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

Following GP1 outlined for compound 4, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) but using 1.0 equiv. of [Ru(bpy)₂(ppy)]PF₆, 1.5 equiv. of piperidine, 1.5 equiv. NCS and 6 equiv. of HClO₄, [Ru(bpy)₂(ppy)]PF₆ (71 mg, 0.1 mmol). After extraction the solvents were removed under vacuum and the crude was dissolved in acetone, treated with an excess of KPF₆ and stirred for 5 min. The mixture was then evaporated to dryness and extracted with CH₂Cl₂ and H₂O. The organic layer was dried (MgSO₄), filtered and evaporated. Purification by column chromatography on silica gel, eluting with DCM/MeOH (from 100:0 to 95:5) gave 106 (29 mg, 37%) as a black solid. FT-IR ν_max (film)/cm^–1 2936, 1598, 1461, 1442, 1065; ¹H NMR (500 MHz, CD₃CN) δ 8.44 (1H, d, J = 8.2 Hz), 8.37 (1H, d, J = 8.1 Hz), 8.30 (2H, t, J = 8.3 Hz), 8.10 (1H, d, J = 5.7 Hz), 8.02 (1H, d, J = 8.0 Hz), 7.97 (1H, t, J = 7.9 Hz), 7.87–7.78 (4H, m), 7.78–7.71 (2H, m), 7.67 (1H, t, J = 7.9 Hz), 7.55 (1H, d, J = 5.7 Hz), 7.48 (1H, bs), 7.44–7.37 (1H, m), 7.21 (3H, q, J = 6.3 Hz), 6.90 (1H, t, J = 6.5 Hz), 6.61 (1H, d, J = 7.2 Hz), 6.24 (1H, d, J = 7.4 Hz), 3.03 (4H, bs), 1.70–1.65 (4H, m), 1.56–1.50 (2H, m); ¹³C NMR (125 MHz, CD₃CN) δ 180.8, 167.9, 158.1, 157.2, 157.1, 155.7, 154.5, 150.7, 150.5, 150.3, 149.5, 148.7, 145.7, 136.5, 135.9, 135.5, 135.1, 133.9, 133.5, 127.4, 126.6, 126.5, 126.3, 123.7, 123.5, 123.3, 123.2, 122.5, 120.5, 119.2, 114.0, 52.2, 26.5, 24.5; HRMS (ESI⁺): Found M⁺ 651.1804, [C₃₆H₃₃N₆Ru]⁺ requires 651.1805.