Organometallics
Article
1 H), 7.05−6.96 (m, 3 H), 6.88 (t, J = 7.3 Hz, 1 H), 5.73 (m, 1 H),
2.84−2.78 (m, 3 H), 2.61−2.57 (m, 2 H), 1.18 (d, J = 6.9 Hz, 3:3 H).
13C{1H} NMR (CDCl3, 100 MHz): δ 140.1, 134.4, 129.6, 128.3,
126.4, 126.2, 124.4, 120.3, 117.8, 103.3, 30.1, 27.4, 22.8, 22.0. HRMS:
calcd for C15H17N 211.1361, found 211.1356.
2-Methyl-5-phenyl-1H-pyrrole (7q): 289 mg, 92% yield, color-
less solid. 1H NMR (CDCl3, 400 MHz): δ 8.14 (s, br, 1 H), 7.49−7.47
(m, 2 H), 7.41−7.37 (m, 2 H), 7.25−7.21 (m, 1 H), 6.49−6.47 (t, J =
3.0 Hz, 1 H), 6.04−6.02 (m, 1 H), 2.37 (s, 3 H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 133.0, 130.9, 129.2, 128.9, 125.7, 123.4, 108.0,
106.3, 13.2.
2-Methyl-5-phenyl-1H-pyrrole (7r): 312 mg, 91% yield, colorless
solid. 1H NMR (CDCl3, 400 MHz): δ 8.16 (s, br, 1 H), 7.48 (d, J = 7.9
Hz, 2 H), 7.39 (t, J = 7.7 Hz, 2 H), 7.22 (t, J = 7.3 Hz, 1 H), 6.48 (t, J
= 2.9 Hz, 1 H), 6.05−6.04 (m, 1 H), 2.73 (q, J = 7.6 Hz, 2 H), 1.34 (t,
J = 7.6 Hz, 3 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 135.8, 133.1,
130.7, 128.9, 125.8, 123.5, 106.4, 106.1, 21.1, 13.7.
141.7, 134.1, 128.7, 126.5, 126.1, 125.6, 115.9, 106.9, 31.4, 30.7, 12.6.
HRMS: calcd for C15H19N 213.1517, found 213.1514.
5-Benzyl-3-methyl-2-phenyl-1H-pyrrole (8e): 297 mg, 60%
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yield, colorless oil. H NMR (CDCl3, 400 MHz): δ 7.65 (s, br, 1 H),
7.28 (m, 2 H), 7.25−7.23 (m, 3 H), 7.19−7.09 (m, 5 H), 5.83 (d, J =
2.8 Hz, 1 H), 3.90 (s, 2 H), 2.17 (s, 3 H). 13C{1H} NMR (CDCl3, 100
MHz): δ 139.4, 133.9, 130.7, 128.9, 128.8, 128.8, 127.6, 126.6, 126.1,
125.7, 116.5, 110.9, 34.3, 12.7.
3-Methyl-2,5-diphenyl-1H-pyrrole (8f): 378 mg, 81% yield,
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white solid. H NMR (CDCl3, 400 MHz): δ 8.30 (s, br, 1 H), 7.53−
7.50 (m, 4 H), 7.47−7.43 (m, 2 H), 7.41−7.37 (m, 2 H), 7.31−7.27
(m, 1 H), 7.25−7.21 (m, 1 H), 6.48 (d, J = 2.8 Hz, 1 H), 2.33 (s, 3 H).
13C{1H} NMR (CDCl3, 100 MHz): δ 133.6, 132.6, 131.6, 129.5,
129.0, 128.9, 126.5, 126.4, 126.3, 123.8, 118.3, 110.1, 12.7.
3-Methyl-2,4,5-triphenyl-1H-pyrrole (8g): 427 mg, 69% yield,
white solid. 1H NMR (CDCl3, 400 MHz): δ 8.24 (s, br, 1 H), 7.62 (m,
2 H), 7.54 (t, J = 7.5 Hz, 2 H), 7.47−7.31 (m, 11 H), 2.31 (s, 3 H).
13C{1H} NMR (CDCl3, 100 MHz): δ 136.2, 133.5, 133.1, 130.7,
128.9, 128.7, 128.4, 126.9, 126.8, 126.5, 126.3, 124.5, 117.1, 11.4.
2-(tert-Butyl)-5-phenyl-1H-pyrrole (7s): 352 mg, 88% yield,
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white solid. H NMR (CDCl3, 400 MHz): δ 8.17 (s, br, 1 H), 7.49−
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1,2-Diphenylethanone (9a): 300 mg, 76% yield, white solid. H
7.47 (m, 2 H), 7.40−7.36 (m, 2 H), 7.22−7.18 (m, 1 H), 6.45−6.44
(m, 1 H), 6.05- 6.03 (m, 1 H), 1.39 (s, 9 H). 13C{1H} NMR (CDCl3,
100 MHz): δ 143.4, 133.2, 130.5, 128.9, 125.8, 123.6, 105.8, 104.6,
31.6, 30.7.
NMR (CDCl3, 400 MHz): δ 7.91 (d, J = 7.6 Hz, 2 H), 7.45−7.42 (m,
1 H), 7.36−7.32 (m, 2 H), 7.24−7.13 (m, 5 H), 4.17 (s, 2 H).
13C{1H} NMR (CDCl3, 100 MHz): δ 197.7, 136.7, 134.6, 133.2,
129.5, 128.7, 128.7, 128.7, 127.0, 45.6.
1-Phenyl-3-(p-tolyl)propan-1-one (9b): 395 mg, 88% yield,
white solid. 1H NMR (CDCl3, 400 MHz): δ 7.85 (d, J = 7.4 Hz, 2 H),
7.45−7.42 (m, 1 H), 7.35−7.31 (m, 2 H), 7.05−6.99 (m, 4 H), 3.17 (t,
J = 7.7 Hz, 2 H), 2.92 (t, J = 7.7 Hz, 2 H), 2.2 (s, 3 H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 199.4, 138.3, 136.9, 135.7, 133.1, 129.3, 128.7,
128.4, 128.1, 40.7, 29.8, 21.1.
2-Benzyl-5-phenyl-1H-pyrrole (7t): 397 mg, 85% yield, colorless
solid. 1H NMR (CDCl3, 400 MHz): δ 8.10 (s, br, 1 H), 7.48−7.33 (m,
9 H), 7.27−7.23 (m, 1 H), 6.56 (t, J = 3.0 Hz, 1 H), 6.16−6.15 (m, 1
H), 4.10 (s, 2 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 139.4, 132.9,
132.1, 131.6, 128.9, 128.8, 128.7, 126.6, 125.9, 123.5, 108.7, 106.2,
34.3.
2,5-Diphenyl-1H-pyrrole (7u): 347 mg, 79% yield, colorless solid.
1H NMR (CDCl3, 400 MHz): δ 8.44 (s, br, 1 H), 7.41 (d, J = 7.7 Hz,
4 H), 7.27 (t, J = 7.7 Hz, 4 H), 7.12 (t, J = 7.0 Hz, 2 H), 6.48 (d, J =
2.3 Hz, 2 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 133.2, 132.6,
129.0, 126.5, 123.9, 108.0.
2,3,5-Triphenyl-1H-pyrrole (7v): 384 mg, 65% yield, white solid.
1H NMR (CDCl3, 400 MHz): δ 8.38 (s, br, 1 H), 7.53 (d, J = 7.5 Hz,
2 H), 7.40−7.18 (m, 13 H), 6.69 (d, J = 2.7 Hz, 1 H). 13C{1H} NMR
(CDCl3, 100 MHz): δ 136.5, 133.2, 132.3, 129.1, 128.8, 128.5, 128.5,
127.6, 127.1, 126.7, 126.1, 123.9, 123.9, 108.7.
1,2-Bis(5-isopropyl-1H-pyrrol-2-yl)ethane (10): 274 mg, 56%
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yield, yellow oil. H NMR (CDCl3, 400 MHz): δ 7.60 (s, br, 2 H),
5.90 (t, J = 2.8 Hz, 2 H), 5.85 (t, J = 2.7 Hz, 2 H), 2.91 (s, 4 H), 2.88−
2.83 (m, 2 H), 1.24 (d, J = 6.9 Hz, 6:6 H). 13C{1H} NMR (CDCl3,
100 MHz): δ 137.9, 130.5, 105.0, 102.7, 28.2, 27.1, 22.8. HRMS: calcd
for C16H24N2 244.1939, found 244.1934.
2-Phenylpyridine (12a): 186 mg, 60% yield, colorless oil. 1H
NMR (CDCl3, 400 MHz): δ 8.71−8.69 (m, 1 H), 8.01−7.99 (m, 2
H), 7.74−7.72 (m, 2 H), 7.50−7.46 (m, 2 H), 7.44−7.41 (m, 1 H),
7.24−7.20 (m, 1 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 157.5,
149.7, 139.5, 136.8, 129.0, 128.8, 127.0, 122.2, 120.7.
5-(Naphthalen-2-yl)-2,3-diphenyl-1H-pyrrole (7w): 484 mg,
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70% yield, colorless solid. mp 187−189 °C. H NMR (CDCl3, 400
2-Methyl-6-phenylpyridine (12b): 196 mg, 58% yield, colorless
MHz): δ 8.54 (s, br, 1 H), 7.90−7.80 (m, 4 H), 7.72−7.70 (m, 1 H),
7.51−7.43 (m, 6 H), 7.36−7.21 (m, 6 H), 6.82 (d, J = 2.8 Hz, 1 H).
13C{1H} NMR (CDCl3, 100 MHz): δ 136.4, 133.9, 133.1, 132.4,
129.9, 129.7, 128.9, 128.8, 128.6, 128.5, 127.9, 127.8, 127.7, 127.2,
126.7, 126.1, 125.7, 124.1, 123.1, 121.2, 109.4. HRMS:calcd for
C26H19N 345.1517, found 345.1515.
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oil. H NMR (CDCl3, 400 MHz): δ 7.88−7.86 (m, 2 H), 7.48 (t, J =
7.7 Hz, 1 H), 7.39−7.32 (m, 3 H), 7.29−7.25 (m, 1 H), 6.95 (d, J =
7.6 Hz, 1 H), 2.51 (s, 3 H). 13C{1H} NMR (CDCl3, 100 MHz): δ
158.4, 157.0, 139.8, 136.9, 128.7, 128.7, 127.0, 121.6, 117.6, 24.8.
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2,6-Diphenylpyridine (12c): 259 mg, 56% yield, white solid. H
NMR (CDCl3, 400 MHz): δ 8.21−8.19 (m, 4 H), 7.84−7.80 (m, 1
H), 7.71 (d, J = 7.6 Hz, 2 H), 7.56−7.52 (m, 4 H), 7.48−7.45 (m, 2
H). 13C{1H} NMR (CDCl3, 100 MHz): δ 156.9, 139.6, 137.6, 129.1,
128.8, 127.1, 118.7.
3,5-Dimethyl-2-phenyl-1H-pyrrole (8a): 274 mg, 80% yield,
colorless oil. 1H NMR (CDCl3, 400 MHz): δ 7.81 (s, br, 1 H), 7.40−
7.37 (m, 4 H), 7.23−7.19 (m, 1 H), 5.85 (s, 1 H), 2.31 (s, 3 H), 2.25
(s, 3 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 134.0, 128.8, 127.6,
126.9, 126.0, 125.6, 116.6, 110.4, 13.1, 12.6.
2-Phenylquinoline (12d): 341 mg, 83% yield, white solid. 1H
NMR (CDCl3, 400 MHz): δ 8.04 (d, J = 8.4 Hz,1 H),8.01−7.99 (m, 2
H), 7.93 (d, J = 8.6 Hz, 1 H), 7.62 (d, J = 8.6 Hz, 1 H), 7.58−7.51 (m,
2 H), 7.36−7.27 (m, 4 H). 13C{1H} NMR (CDCl3, 100 MHz): δ
157.3, 148.3, 139.6, 136.7, 129.7, 129.6, 129.3, 128.8, 127.6, 127.5,
127.1, 126.2, 118.9.
5-Ethyl-3-methyl-2-phenyl-1H-pyrrole (8b): 315 mg, 85%
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yield, colorless oil. H NMR (CDCl3, 400 MHz): δ 7.74 (s, br, 1
H), 7.33−7.27 (m, 4 H), 7.14−7.10 (m, 1 H), 5.78 (d, J = 2.6 Hz, 1
H), 2.56 (q, J = 7.4 Hz, 2 H), 2.17 (s, 3 H), 1.19 (t, J = 7.6 Hz, 3 H).
13C{1H} NMR (CDCl3, 100 MHz): δ 134.1, 128.8, 128.1, 126.7,
126.1, 125.6, 116.4, 108.7, 21.0, 13.7, 12.7.
6,7,8,9-Tetrahydro-5H-cyclohepta[b]pyridine (13a): 271 mg,
92% yield, colorless oil. 1H NMR (CDCl3, 400 MHz): δ 8.21 (dd, J =
4.9, 1.5 Hz, 1 H), 7.29 (dd, J = 7.4, 1.2 Hz, 1 H), 6.95−6.92 (m, 1 H),
2.99−2.96 (m, 2 H), 2.70−2.68 (m, 2 H), 1.83−1.77 (m, 2 H), 1.66−
1.56 (m, 4 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 163.2, 146.1,
138.1, 136.4, 121.1, 39.4, 35.3, 32.5, 27.9, 26.4.
2-Methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine
(13b): 242 mg, 75% yield, colorless oil. 1H NMR (CDCl3, 400 MHz):
δ 7.19 (d, J = 7.6 Hz, 1 H), 6.79 (d, J = 7.6 Hz, 1 H), 2.95−2.92 (m, 2
H), 2.67−2.64 (m, 2 H), 2.41 (s, 3 H), 1.82−1.76 (m, 2 H), 1.63−1.55
(m, 4 H). 13C{1H} NMR (CDCl3, 100 MHz): δ 162.6, 154.5, 137.0,
134.9, 120.6, 39.5, 35.0, 32.7, 28.2, 26.7, 24.1.
5-Isopropyl-3-methyl-2-phenyl-1H-pyrrole (8c): 327 mg, 82%
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yield, colorless oil. H NMR (CDCl3, 400 MHz): δ 7.91 (s, br, 1 H),
7.51−7.46 (m, 4 H), 7.32−7.28 (m, 1 H), 5.98 (d, J = 2.7 Hz, 1 H),
3.08−2.97 (m, 1 H), 2.36 (s, 3 H), 1.39 (d, J = 6.9 Hz, 6 H). 13C{1H}
NMR (CDCl3, 100 MHz): δ 138.8, 134.1, 128.7, 126.6, 126.1, 125.6,
116.1, 107.4, 27.2, 22.8, 12.7.
5-(tert-Butyl)-3-methyl-2-phenyl-1H-pyrrole (8d): 324 mg,
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76% yield, colorless oil. H NMR (CDCl3, 400 MHz): δ 7.74 (s, br,
1 H), 7.32−7.26 (m, 4 H), 7.12−7.08 (m, 1 H), 5.78 (d, J = 2.9 Hz, 1
H), 2.16 (s, 3 H), 1.23 (s, 9 H). 13C{1H} NMR (CDCl3, 100 MHz): δ
F
Organometallics XXXX, XXX, XXX−XXX