Page 17 of 20
The Journal of Organic Chemistry
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Synthesized in accordance with the general procedure using tetrazole 3g (39.2 mg, 0.20 mmol), phenylboronic acid (49 mg,
0.4 mmol), copper(I) oxide (1.4 mg, 10 μmol) and DMSO (2 mL) to yield 5-(naphthalen-2-yl)-2-phenyl-2H-tetrazole (46.4
mg, 0.17 mmol, 85 % yield) as a beige solid.
1H NMR (500 MHz, CDCl3) δ 8.80 (s, 1H), 8.32 (dd, J = 8.5, 1.6 Hz, 1H), 8.26 – 8.22 (m, 2H), 8.02 – 7.97 (m, 2H), 7.92 – 7.87
(m, 1H), 7.61 – 7.54 (m, 4H), 7.51 (app. t, J = 7.4 Hz, 1H).
13C{1H} NMR (126 MHz, CDCl3) δ 165.5, 137.1, 134.5, 133.4, 129.81, 129.77, 128.93, 128.87, 128.0, 127.4, 127.1, 126.9,
124.6, 124.1, 120.0.
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HRMS (ESI) m/z: [M+H]+ Calcd for C17H13N4 273.1140; Found 273.1143.
IR νmax (neat): 3051, 2930 2853, 1595, 1522, 1503, 1468, 1436 cm-1
2,5-di(naphthalen-2-yl)-2H-tetrazole (4k)
Synthesized in accordance with the general procedure using tetrazole 3g (39.2 mg, 0.20 mmol), 2-naphthylboronic acid (69
mg, 0.4 mmol), copper(I) oxide (1.4 mg, 10 μmol) and DMSO (2 mL) to yield 2,5-di(naphthalen-2-yl)-2H-tetrazole (10.2 mg,
0.03 mmol, 16 % yield) as a white solid.
1H NMR (400 MHz, CDCl3) δ 8.85 (s, 1H), 8.72 (d, J = 1.7 Hz, 1H), 8.39 (dd, J = 4.5, 1.8 Hz, 1H), 8.37 (dd, J = 4.1, 1.8 Hz, 1H),
8.07 (d, J = 9.0 Hz, 1H), 8.05 – 7.99 (m, 3H;), 7.97 – 7.90 (m, 2H;), 7.66 – 7.55 (m, 4H).
13C{1H} NMR (101 MHz, CDCl3) δ 165.6, 134.6, 134.5, 133.6, 133.4, 133.3, 130.1, 129.0, 128.9, 128.85, 128.2, 128.1, 127.7,
127.6, 127.4, 127.2, 126.9, 124.6, 124.2, 118.5, 118.1.
HRMS (ESI) m/z: [M+H]+ Calcd for C21H15N4 323.1297; Found 323.1299.
IR νmax (neat): 3055, 3030, 1630, 1603, 1524, 1501, 1474, 1437 cm-1
5-(naphthalen-2-yl)-2-(o-tolyl)-2H-tetrazole (4l)
Synthesized in accordance with the general procedure using tetrazole 3g (39.2 mg, 0.20 mmol), o-tolylboronic acid (54 mg,
0.4 mmol), copper(I) oxide (1.4 mg, 10 μmol) and DMSO (2 mL) to yield 5-(naphthalen-2-yl)-2-(o-tolyl)-2H-tetrazole (20.0
mg, 0.07 mmol, 35 % yield) as a beige solid.
1H NMR (500 MHz, CDCl3) δ 8.80 (s, 1H), 8.32 (dd, J = 8.5, 1.6 Hz, 1H), 8.00 (d, J = 8.5 Hz, 1H), 8.00 – 7.97 (m, 1H), 7.93 –
7.88 (m, 1H), 7.71 (d, J = 7.9 Hz, 1H), 7.59 – 7.53 (m, 2H), 7.51 – 7.39 (m, 3H), 2.47 (s, 3H).
13C{1H} NMR (126 MHz, CDCl3) δ 165.2, 136.7, 134.5, 133.4, 133.3, 132.1, 130.5, 129.0, 128.9, 128.0, 127.3, 127.07 ,
127.05, 126.9, 125.4, 124.7, 124.1, 19.0.
HRMS (ESI) m/z: [M+H]+ Calcd for C18H15N4 287.1297; Found 287.1299.
IR νmax (neat): 3061, 2924, 2853, 1605, 1522, 1493, 1464, 1435 cm-1
2-phenyl-5-(o-tolyl)-2H-tetrazole (4m)
Synthesized in accordance with the general procedure using tetrazole 3f (32.0 mg, 0.20 mmol), phenylboronic acid (49 mg,
0.4 mmol), copper(I) oxide (1.4 mg, 10 μmol) and DMSO (2 mL) to yield 2-phenyl-5-(o-tolyl)-2H-tetrazole (32.0 mg, 0.14
mmol, 68 % yield) as an off-white solid.
1H NMR (400 MHz, DMSO) δ 8.19 – 8.13 (m, 2H), 8.04 (dd, J = 7.6, 1.2 Hz, 1H), 7.73 – 7.66 (m, 2H), 7.64 – 7.59 (m, 1H), 7.50
– 7.36 (m, 3H), 2.64 (s, 3H).
13C{1H} NMR (101 MHz, DMSO) δ 164.9, 137.0, 136.2, 131.5, 130.4, 130.1, 129.2, 126.3, 125.6, 119.9, 21.2, 1C not
observed.
HRMS (ESI) m/z: [M+H]+ Calcd for C14H13N4 237.1135; Found 237.1134.
IR νmax (neat): 3076, 3030, 2980, 2959, 2926, 1595, 1522, 1497, 1479, 1456, 1418 cm-1
N-(4-(5-(o-tolyl)-2H-tetrazol-2-yl)phenyl)acetamide (4n)
Synthesized in accordance with the general procedure using tetrazole 3f (32.0 mg, 0.20 mmol), (4-
acetamidophenyl)boronic acid (71.6 mg, 0.4 mmol), copper(I) oxide (1.4 mg, 10 μmol) and DMSO (2 mL) to yield N-(4-(5-(o-
tolyl)-2H-tetrazol-2-yl)phenyl)acetamide (41.2 mg, 0.14 mmol, 71 % yield) as a white solid.
1H NMR (400 MHz, CDCl3) δ 8.17 – 8.13 (m, 2H), 8.13 – 8.09 (m, 1H), 7.75 (d, J = 8.9 Hz, 2H), 7.56 (br. s, 1H), 7.43 – 7.31 (m,
3H), 2.71 (s, 3H), 2.23 (s, 3H).
13C{1H} NMR (101 MHz, CDCl3) δ 168.6, 165.7, 139.3, 137.8, 133.0, 131.6, 130.3, 129.7, 126.3, 126.2, 120.7, 120.5, 24.8,
21.9.
HRMS (ESI) m/z: [M+H]+ Calcd for C16H16N5O 294.1349; Found 294.1351.
IR νmax (neat): 3294, 3269, 3211, 3148, 3075, 2957, 2926, 1661, 1611, 1535, 1510, 1481, 1450, 1414cm-1
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