The Journal of Organic Chemistry
Page 6 of 10
5-(3-Phenylpropyl)pyrimidine (11g). Ligand 4: 19 h, 95%
yield. Colorless oil. H NMR (500 MHz, CDCl3) δ 9.07 (s,
2H), 7.18 (m, 3H), 6.68 (d, J = 7.2 Hz, 1H), 6.53 (d, J = 8.3
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Hz, 1H), 3.92 (s, 3H), 2.72 (t, J = 7.6 Hz, 2H), 2.67 (t, J = 7.7
Hz, 2H), 2.07 (m, 2H). 13C NMR (126 MHz, CDCl3) δ
159.7, 142.4, 138.6, 128.5, 128.2, 125.7, 115.2, 107.3, 53.1,
37.2, 35.4, 30.8. HRMS (ESI-TOF) (m/z): [M + H]+ calcd
for C15H18NO, 228.1388; found 228.1376.
1H), 8.57 (s, 2H), 7.30 (m, 2H), 7.19 (m, 3H), 2.69 (t, J =
7.6 Hz, 1H), 2.64 (t, J = 7.6 Hz, 1H), 2.02~1.96 (m, 2H). 13C
NMR (101 MHz, CDCl3) δ 156.7, 156.6, 141.0, 134.9,
128.4, 128.3, 126.0, 35.1, 32.0, 29.7. HRMS (ESI-TOF)
(m/z): [M + H]+ calcd for C13H15N2, 199.1235; found
199.1232.
2-(Benzyloxy)-6-(3-phenylpropyl)pyridine (13c). Ligand 1:
26 h, 77% yield (from 2.0 equiv of (3-bromopropyl)benzene,
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6-(3-Phenylpropyl)-[1,2,4]triazolo[1,5-a]pyridine (11h).
5 mol% NiI2). Colorless oil. H NMR (500 MHz, CDCl3) δ
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Ligand 4: 24 h, 74% yield. Pale yellow oil. H NMR (500
7.45 (m, 3H), 7.35 (m, 2H), 7.28 (m, 3H), 7.18 (d, J = 7.4
Hz, 3H), 6.69 (d, J = 7.2 Hz, 1H), 6.60 (d, J = 8.2 Hz, 1H),
5.38 (s, 2H), 2.72 (t, J = 7.5 Hz, 2H), 2.65 (t, J = 7.5 Hz, 2H),
MHz, cdcl3) δ 8.38 (s, 1H), 8.30 (s, 1H), 7.68 (d, J = 9.1 Hz,
1H), 7.37 (dd, J = 9.1, 1.4 Hz, 1H), 7.30 (m, 2H), 7.20 (m,
3H), 2.70 (m, 4H), 2.05~1.99 (m, 2H). 13C NMR (126
MHz, CDCl3) δ 153.4, 149.1, 141.1, 131.3, 128.2 (2), 128.1,
128.1, 126.1, 125.8, 115.9, 34.8, 31.8, 31.5. HRMS (ESI-
TOF) (m/z): [M + H]+ calcd for C15H16N3, 238.1344; found
238.1340.
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2.09~2.03 (m, 2H). C NMR (126 MHz, CDCl3) δ 163.1,
159.6, 142.4, 138.7, 137.8, 128.5, 128.3, 128.3, 128.1, 127.6,
125.7, 115.4, 107.9, 67.3, 37.2, 35.4, 30.8. HRMS (ESI-TOF)
(m/z): [M + H]+ calcd for C21H21NO, 304.1701; found
304.1693.
3-(3-Phenylpropyl)-1,5-naphthyridine (11i). Ligand 4: 17 h,
5-Methoxy-2-(3-phenylpropyl)pyridine (13d). Ligand 1: 22
52% yield (from 2.0 equiv. of (3-chloropropyl)benzene, 7
h, 65% yield (from 2.0 equiv of (3-bromopropyl)benzene, 5
1
1
mol% catalysts). Colorless oil. H NMR (500 MHz, CDCl3)
mol% NiI2). Colorless oil. H NMR (500 MHz, CDCl3) δ
δ 8.96 (dd, J = 4.1, 1.4 Hz, 1H), 8.84 (d, J = 1.8 Hz, 1H), 8.38
(d, J = 8.4 Hz, 1H), 8.18 (s, 1H), 7.60 (dd, J = 8.5, 4.2 Hz,
1H), 7.30 (m, 2H), 7.21 (m, 3H), 2.90 (t, J = 7.7 Hz, 2H),
8.23 (d, J = 2.4 Hz, 1H), 7.26 (m, 2H), 7.17 (m, 3H), 7.10
(m, 1H), 7.03 (d, J = 8.5 Hz, 1H), 3.80 (s, 3H), 2.77 (t, J =
7.7 Hz, 2H), 2.66 (t, J = 7.7 Hz, 2H), 2.06~2.00 (m, 2H). 13C
NMR (126 MHz, CDCl3) δ 153.88, 142.10, 136.32, 128.35,
128.17, 125.61, 122.69, 121.12, 55.47, 55.45, 36.73, 35.39,
31.56. HRMS (ESI-TOF) (m/z): [M + H]+ calcd for
C15H18NO, 228.1388; found 228.1378.
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2.73 (t, J = 7.6 Hz, 2H), 2.15~2.08 (m, 2H). C NMR (126
MHz, CDCl3) δ 152.8, 151.1, 143.8, 142.1, 141.4, 138.8,
137.1, 135.4, 128.4, 128.4, 126.0, 123.6, 35.1, 32.5, 32.2.
HRMS (ESI-TOF) (m/z): [M + H]+ calcd for C17H17N2,
249.1392; found 249.1375.
5-Fluoro-2-(3-phenylpropyl)pyridine (13e). Ligand 1: 20 h,
1-Methyl-6-(3-phenylpropyl)-1H-pyrazolo[4,3-b]pyridine
83% yield (from 2.0 equiv of (3-bromopropyl)benzene at
1
(11j). Ligand 4: 24 h, 51% yield (from 2.0 equiv. of (3-
40oC, 5 mol% NiI2). White solid. mp 98-100oC H NMR
1
chloropropyl)benzene, 7 mol% catalysts). Pale yellow oil. H
(500 MHz, CDCl3) δ 8.37 (d, J = 2.1 Hz, 1H), 7.26 (m, 3H),
7.18~7.15 (m, 3H), 7.08 (dd, J = 8.5, 4.3 Hz, 1H), 2.80 (t, J =
7.7 Hz, 2H), 2.66 (t, J = 7.7 Hz, 2H), 2.07~2.01 (m, 2H). 13C
NMR (126 MHz, CDCl3) δ 157.9 (d, J = 253.3 Hz), 157.8
(d, J = 8.8 Hz), 141.8, 137.1 (d, J = 20.4 Hz), 128.3, 128.2,
125.7, 123.3, 122.9 (d, J = 17.6 Hz), 36.9, 35.3, 31.4. 19F
NMR (377 MHz, CDCl3) δ 0.5. HRMS (ESI-TOF) (m/z):
[M + H]+ calcd for C14H15FN, 216.1189; found 216.1179.
NMR (401 MHz, CDCl3) δ 8.43 (d, J = 1.4 Hz, 1H), 8.17 (s,
1H), 7.49 (s, 1H), 7.30 (m, 2H), 7.20 (m, 3H), 4.05 (s, 3H),
2.82 (t, J = 7.6 Hz, 2H), 2.70 (t, J = 7.6 Hz, 2H), 2.05 (m,
2H). 13C NMR (101 MHz, CDCl3) δ 147.0, 141.5, 140.3,
135.0, 133.3, 133.0, 128.5, 128.4, 128.3, 125.9, 115.5, 35.7,
35.3, 32.9. HRMS (ESI-TOF) (m/z): [M + H]+ calcd for
C16H18N3, 252.1501; found 252.1486.
2-(3-Phenylpropyl)pyridine (13a). Ligand 4: 18 h, 46%
yield; Ligand 5: 22 h, 50% yield; Ligand 1: 5 h, 85% yield
(from 2.0 equiv of (3-bromopropyl)benzene, 5 mol% NiI2).
4-Methyl-2-(3-phenylpropyl)pyridine (13f). Ligand 1: 15 h,
90% yield (from 2.0 equiv of (3-bromopropyl)benzene, 5
1
mol% NiI2). Pale yellow oil. H NMR (401 MHz, CDCl3) δ
1
Colorless oil. H NMR (500 MHz, CDCl3) δ 8.53 (d, J = 4.4
8.37 (d, J = 5.0 Hz, 1H), 7.26 (m, 2H), 7.20~7.17 (m, 3H),
6.94 (s, 1H), 6.91 (d, J = 5.0 Hz, 1H), 2.78 (t, J = 8.0 Hz,
2H), 2.68 (t, J = 8.0 Hz, 2H), 2.30 (s, 3H), 2.09~2.02 (m,
2H). 13C NMR (101 MHz, CDCl3) δ 161.7, 149.0, 147.2,
142.2, 128.4, 128.2, 125.7, 123.6, 122.0, 37.8, 35.6, 31.5,
20.9. HRMS (ESI-TOF) (m/z): [M + H]+ calcd for
C15H18N, 212.1439; found 212.1428.
Hz, 1H), 7.57 (td, J = 7.7, 1.4 Hz, 1H), 7.27 (m, 2H), 7.18
(m, 3H), 7.13 (d, J = 7.8 Hz, 1H), 7.09 (dd, J = 7.2, 5.2 Hz,
1H), 2.83 (t, J = 7.6 Hz, 2H), 2.68 (t, J = 7.6 Hz, 2H),
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2.10~2.04 (m, 2H). C NMR (126 MHz, CDCl3) δ 161.9,
149.2, 142.1, 136.3, 128.4, 128.3, 125.7, 122.7, 121.0, 37.9,
35.5, 31.5. HRMS (ESI-TOF) (m/z): [M + H]+ calcd for
C14H16N, 198.1283; found 198.1278.
5-Fluoro-2-(oxetan-3-yl)pyridine (14a). Ligand 1: 14 h,
2-Methoxy-6-(3-phenylpropyl)pyridine (13b). Ligand 5: 22
h, 64% yield (from 2.0 equiv of (3-chloropropyl)benzene, 7
mol% catalyst); Ligand 1: 20 h, 76% yield (from 2.0 equiv of
50% yield (NiI2 was used in place of NiCl2(dme)). White
1
solid. mp 118-120 °C H NMR (401 MHz, CDCl3) δ 8.49
(d, J = 2.8 Hz, 1H), 7.39 (td, J = 8.4, 2.9 Hz, 1H), 7.27 (dd, J
= 8.6, 4.3 Hz, 1H), 5.06 (dd, J = 8.4, 5.9 Hz, 2H), 4.91 (t, J =
6.2 Hz, 2H), 4.42~4.34 (m, 1H). 13C NMR (101 MHz,
1
(3-bromopropyl)benzene, 5 mol% NiI2). Colorless oil. H
NMR (500 MHz, CDCl3) δ 7.44 (t, J = 7.7 Hz, 1H), 7.27 (m,
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