Compound 107
[Rh(dtbbpy)2(4-azetidyl-ppy)2]PF6
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C but using 1.0 equiv. of [Rh(ppy)2(dtbby)]PF6, 2.5 equiv. of azetidine, 2.5 equiv. of DIPEA, 2.5 equiv. NCS and 10 equiv. of HClO4, [Rh(ppy)2(dtbby)]PF6 (83 mg, 0.1 mmol) gave 107 (16 mg, 17%) as a yellow solid.iii FT-IR νmax (film)/cm–1 2962, 1606, 1556, 1581, 1465, 1435, 1321, 1162, 1061; 1H NMR (500 MHz, CD3CN) δ 8.47 (2H, d, J = 1.8 Hz), 7.98 (2H, d, J = 5.7 Hz), 7.77 (2H, d, J = 8.2 Hz), 7.73 (2H, ddd, J = 8.4, 7.2, 1.6 Hz), 7.62 (2H, d, J = 8.4 Hz), 7.54 (2H, dd, J = 5.7, 1.9 Hz), 7.39 (2H, d, J = 6.1 Hz), 6.83 (2H, ddd, J = 7.3, 5.8, 1.6 Hz), 6.14 (2H, dd, J = 8.4, 2.3 Hz), 5.24 (2H, d, J = 2.3 Hz), 3.67–3.59 (8H, m), 2.22 (4H, quint, J = 7.3 Hz), 1.42 (18H, s); 13C NMR (125 MHz, CD3CN) δ 170.6, 166.1, 164.6, 155.0, 153.1, 150.2, 149.0, 138.2, 132.8, 126.1, 125.2, 121.5, 120.9, 118.6, 113.7, 106.5, 51.7, 36.0, 30.1, 16.7; HRMS (ESI+): Found M+ 789.3135, [C46H50N6Rh]+ requires 789.3147.
