Vogels et al.
1117
1
852, 706. H NMR (in CDCl3) δ: 8.53 (s, 1H), 8.28 (s, 1H),
1143, 1073, 965, 863, 706. 1H NMR (in CDCl3) δ: 7.36–7.31
(ov m, 5H), 7.18–7.15 (ov m, 3H), 6.73 (m, 1H), 4.35 (s,
2H), 1.33 (s, 12H). 13C NMR δ: 147.5, 139.3, 130 (br, C-B),
128.6, 128.5, 127.4, 127.1, 123.9, 119.1, 115.3, 83.5, 48.1,
24.7. 11B NMR δ: 31.8 (br). Anal. calcd. for C19H24NO2B: C
73.79, H 7.84, N 4.53; found: C 73.80, H 7.59, N 4.73.
8.07 (d, J = 8 Hz, 1H), 7.93 (d, J = 8 Hz, 1H), 7.69 (d, J =
8 Hz, 1H), 7.64 (s, 1H), 7.48 (t, J = 8 Hz, 1H), 7.45–7.33
(ov m, 2H), 1.36 (s, 24H). 13C NMR δ: 160.4, 151.5, 137.6,
135.9, 135.6, 132.2, 130.9, 129.7 (br, C-B), 128.6, 128.2,
126.1, 124.8, 84.0, 24.9. 11B NMR δ: 31.5 (br).
1g
2b
Yield: 92% of an off-white solid; mp 208°C. IR (Nujol):
2971, 2910, 1710, 1623, 1608, 1511, 1465, 1355, 1271,
1142, 1087, 964, 855, 702. H NMR (in CDCl3) δ: 8.52 (s,
Yield: 58% of a yellow solid; mp 125°C. IR (Nujol):
3418, 2971, 2883, 1599, 1579, 1518, 1459, 1342, 1140, 846,
1
1
709. H NMR (in CDCl3) δ: 8.19 (d, J = 8 Hz, 2H), 7.53 (d,
1H), 7.90 (s, 4H), 7.70 (d, J = 8 Hz, 1H), 7.64 (s, 1H), 7.42–
7.36 (ov m, 2H), 1.36 (s, 24H). 13C NMR δ: 160.6, 151.5,
138.7, 135.3, 132.7, 132 (br, C-B), 129 (br, C-B), 128.8,
128.2, 126.2, 125.1, 84.1, 25.1. 11B NMR δ: 31.5 (br).
J = 8 Hz, 2H), 7.19–7.12 (ov m, 3H), 6.64 (m, 1H), 4.48 (s,
2H), 1.33 (s, 12H). 13C NMR δ: 147.5, 147.1, 146.7, 130 (br,
C-B), 128.9, 127.8, 124.6, 123.8, 119.4, 115.3, 83.8, 47.5,
24.8. 11B NMR δ: 32.3 (br). Anal. calcd. for C19H23N2O4B:
C 64.41, H 6.56, N 7.91; found: C 64.75, H 6.40, N 8.16.
1h
Yield: 81% of an off-white solid; mp 209°C. IR (Nujol):
2969, 2889, 1606, 1572, 1462, 1413, 1354, 1268, 1141,
1066, 965, 852, 739, 705. H NMR (in CDCl3) δ: 9.70 (s,
1H), 8.76 (d, J = 8 Hz, 2H), 8.55 (s, 1H), 8.06 (d, J = 8 Hz,
2H), 7.85 (s, 1H), 7.80 (d, J = 8 Hz, 1H), 7.59–7.48 (ov m,
6H), 1.39 (s, 12H). 13C NMR δ: 159.8, 152.0, 132.6, 131.1,
130.5, 130.4, 130 (br, C-B), 128.9, 128.7, 127.2, 127.1,
126.1, 125.3, 124.9, 124.7, 83.9, 24.8. 11B NMR δ: 31.4 (br).
2c
Yield: 80% of an off-white solid; mp 105°C. IR (Nujol):
3398, 2974, 2875, 1604, 1579, 1512, 1462, 1363, 1236,
1138, 1086, 1026, 847, 706. 1H NMR (in CDCl3) δ: 7.31 (d,
J = 8 Hz, 2H), 7.22 (ov m, 2H), 7.17 (s, 1H), 6.91 (d, J =
8 Hz, 2H), 6.76–6.71 (m, 1H), 4.29 (s, 2H), 3.82 (s, 3H),
1.35 (s, 12H). 13C NMR δ: 158.8, 147.6, 131.4, 130 (br, C-
B), 128.9, 128.7, 124.0, 119.2, 115.5, 114.0, 83.7, 55.3,
47.8, 24.8. 11B NMR δ: 32.6 (br). Anal. calcd. for
C20H26NO3B: C 70.81, H 7.74, N 4.13; found: C 71.17, H
7.88, N 4.42.
1
1i
Yield: 89% of an off-white solid; mp 176°C. IR (Nujol):
2974, 2881, 1628, 1575, 1484, 1424, 1358, 1321, 1145,
1
1073, 965, 909, 856, 807, 708. H NMR (in CDCl3) δ: 8.56
2d
(s, 2H), 8.39 (s, 1H), 8.04 (d, J = 8 Hz, 2H), 7.73–7.69
(ov m, 4H), 7.55 (t, J = 8 Hz, 1H), 7.45–7.36 (ov m, 4H),
1.37 (s, 24H). 13C NMR δ: 159.6, 151.3, 137.0, 132.7, 131.2,
130 (br, C-B), 129.5, 129.3, 128.8, 126.3, 124.9, 84.0, 25.0.
11B NMR δ: 31.0 (br).
Yield: 70% of a white solid; mp 126°C. IR (Nujol): 3397,
2967, 2883, 1603, 1581, 1511, 1464, 1376, 1273, 1142,
1086, 857, 707. H NMR (in CDCl3) δ: 7.26–7.17 (ov m,
2H), 7.11 (m, 1H), 6.89 (s, 2H), 6.77 (m, 1H), 4.21 (s, 2H),
2.33 (s, 6H), 2.29 (s, 3H), 1.35 (s, 12H). 13C NMR δ: 148.0,
137.5, 137.2, 132.4, 130 (br, C-B), 129.0, 128.7, 123.7,
118.2, 115.6, 83.7, 42.4, 24.8, 20.9, 19.4. 11B NMR δ: 33.0
(br). Anal. calcd. for C22H30NO2B: C 75.20, H 8.62, N 3.99;
found: C 74.89, H 8.59, N 4.08.
1
1j
Yield: 37% of a pale yellow solid; mp 149–152°C. IR
(Nujol): 2916, 2856, 1630, 1460, 1375, 1321, 1273, 1207,
1
1142, 1095, 1016. H NMR (in CDCl3) δ: 7.96–7.86 (ov m,
4H), 7.55 (d, J = 8 Hz, 1H), 7.36 (t, J = 8 Hz, 1H), 7.25 (s,
1H), 6.92 (d, J = 8 Hz, 1H), 2.22 (s, 3H), 1.37 (s, 12H), 1.34
(s, 12H). 13C NMR δ: 165.6, 151.0, 141.9, 134.7, 131 (br, C-
B), 129.7, 128.4, 126.3, 125.3, 122.3, 83.8, 24.9, 17.6. 11B
NMR δ: 30.9 (br).
2e
Yield: 78% of a white solid; mp 138°C. IR (Nujol): 3429,
2943, 2868, 1603, 1581, 1518, 1452, 1377, 1350, 1142, 964,
852, 706. H NMR (in CDCl3) δ: 7.85 (d, J = 8 Hz, 1H),
7.38–7.33 (ov m, 2H), 7.25 (t, J = 8 Hz, 1H), 7.18–7.16
(ov m, 3H), 6.75 (m, 1H), 4.55 (s, 2H), 1.33 (s, 12H), 1.32
(s, 12H). 13C NMR δ: 147.8, 145.7, 136.1, 130.9, 129 (br, C-
B), 128.5, 128.3, 128 (br, C-B), 126.4, 123.6, 119.6, 115.8,
83.6, 83.4, 48.2, 24.8. 11B NMR δ: 31.9 (br). Anal. calcd. for
C25H35NO4B2: C 68.99, H 8.12, N 3.22; found: C 69.27, H
8.06, N 3.39.
1
Synthesis of amines
Catecholborane (1.2 mmol) in 5 mL of toluene was added
dropwise to a stirred solution of the imine (1.0 mmol) in
10 mL of toluene under an atmosphere of dinitrogen. The re-
action was allowed to proceed for 24 h at which point water
(5 mL) was added. The organic phase was extracted and the
corresponding amine was isolated by flash chromatography
through alumina followed by removal of solvent. Con-
versely, formation of the amine could also be achieved by
reduction of the imine with 3 equiv of NaBH4 in 10 mL of
methanol, followed by an organic extraction with Et2O and
filtration.
2f
Yield: 74% of a white solid; mp 166°C. IR (Nujol): 3361,
2970, 2868, 1606, 1583, 1522, 1460, 1363, 1144, 1090, 964,
852, 708. 1H NMR (in CDCl3) δ: 7.78 (s, 1H), 7.70 (d, J =
8 Hz, 1H), 7.44 (d, J = 8 Hz, 1H), 7.30 (t, J = 5 Hz, 1H),
7.15–7.10 (ov m, 3H), 6.67 (m, 1H), 4.29 (s, 2H), 1.31 (s,
12H), 1.29 (s, 12H). 13C NMR δ: 147.5, 138.7, 134.0, 133.6,
130.6, 129 (br, C-B), 128.7, 128.0, 123.9, 119.3, 115.4, 83.8,
83.6, 48.3, 24.8. 11B NMR δ: 31.4 (br). Anal. calcd. for
2a
Yield: 78% of a white solid; mp 86°C. IR (Nujol): 3416,
2969, 2885, 1602, 1582, 1515, 1447, 1353, 1320, 1274,
© 2001 NRC Canada