5
7.48–7.38 (m, 4H), 7.09 (m, 4H), 4.89 (q, J = 7.2 Hz, 1H), 2.57–
HRMS (ESI) m/z calcd for C16H14S [M+H]+ 239.0889, found
239.0889.
ACCEPTED MANUSCRIPT
2.48 (m, 2H), 1.74 (d, J = 7.2 Hz, 3H), 1.60–1.53 (m, 2H), 1.30
(dd, 4H), 0.87 (t, J = 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ
143.85, 142.06, 140.64, 134.11, 131.86, 128.89, 128.53, 127.60,
126.99, 125.94, 125.50, 124.42, 124.14, 40.25, 35.65, 31.76,
31.29, 22.71, 14.18; HRMS (ESI) m/z calcd for C23H26 [M+H]+
303.2107, found 303.2101.
4.10. 1-(1-([1,1'-biphenyl]-4-yl)ethyl)naphthalene [2k]
1
White solid, 70% yield, M.p. 122.7-122.9 °C; H NMR (400
MHz, CDCl3) δ 8.08 (dd, J = 6.2, 3.7 Hz, 1H), 7.86 (dd, J = 6.4,
3.4 Hz, 1H), 7.77 (dd, J = 6.4 Hz, 1H), 7.57–7.37 (m, 10H),
7.34–7.28 (m, 3H), 4.98 (q, J = 7.2 Hz, 1H), 1.81 (d, J = 7.2 Hz,
3H); 13C NMR (101 MHz, CDCl3) δ 148.02, 145.74, 142.01,
141.07, 134.12, 129.26, 128.95, 128.51, 127.05, 125.97, 125.63,
125.46, 124.42, 124.29, 124.12, 122.59, 40.02, 22.71; HRMS
(ESI) m/z calcd for C24H20 [M+H]+ 309.1638, found 309.1631.
4.4. 1-(1-(4-propylphenyl)ethyl)naphthalene [2d]
1
Colourless liquid, 77% yield; H NMR (400 MHz, CDCl3) δ
8.16–8.10 (m, 1H), 7.92–7.86 (m, 1H), 7.78 (d, J = 7.6 Hz, 1H),
7.54–7.43 (m, 4H), 7.24–7.08 (m, 4H), 4.96 (q, 1H), 2.59 (dd,
2H), 1.81 (d, J = 7.2 Hz, 3H), 1.70–1.61 (m, 2H), 0.98 (td, J = 7.2,
3H); 13C NMR (101 MHz, CDCl3) δ 142.04, 140.36, 128.88,
128.60, 128.60, 127.57, 126.99, 125.93, 125.58, 125.40, 124.41,
124.13, 40.25, 37.77, 24.64, 22.73, 14.06; HRMS (ESI) m/z
calcd for C21H22 [M+H]+ 275.1794, found 275.1792.
4.11. 1-(1-(naphthalen-2-yl)ethyl)naphthalene [2l]
1
Light yellow solid, 52% yield, M.p. 88.4-89.2 °C; H NMR
(400 MHz, CDCl3) δ 8.19–8.06 (m, 1H), 7.87 (dd, J = 6.4, 3.4 Hz,
1H), 7.82–7.69 (m, 5H), 7.54–7.33 (m, 7H), 5.11 (q, J = 7.2 Hz,
1H), 1.87 (dd, J = 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ
144.28, 141.63, 134.15, 133.72, 132.22, 128.94, 128.17, 127.85,
127.70, 127.21, 126.95, 126.06, 126.02, 125.66, 125.61, 125.49,
125.46, 124.74, 124.09, 40.83; 22.56; HRMS (ESI) m/z calcd for
C22H18 [M+H]+ 283.1481, found 283.1482.
4.5. 1-(1-(4-(trifluoromethyl)phenyl)ethyl)naphthalene [2f]
1
Colourless liquid, 50% yield; H NMR (400 MHz, CDCl3) δ
8.00–7.72 (m, 3H), 7.54–7.28 (m, 8H), 4.96 (q, J = 7.2 Hz, 1H),
1.77 (d, J = 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 150.92,
140.55, 134.18, 131.66, 129.06, 128.04, 127.56, 126.23, 125.64,
125.59, 125.54, 124.54, 123.82, 40.64, 22.49; HRMS (ESI) m/z
calcd for C19H15F [M+H]+ 301.1199, found 301.1192.
4.12. 9-(4-(1-(naphthalen-1-yl)ethyl)phenyl)-9H-carbazole [2m]
1
White solid, 75% yield, M.p. 166.7-167.1 °C; H NMR (400
MHz, CDCl3) δ 8.15–8.10 (m, 3H), 7.89 (dd, J = 6.4, 3.1 Hz, 1H),
7.83–7.77 (m, 1H), 7.55–7.22 (m, 14H), 5.06 (q, J = 7.2 Hz, 1H),
1.87 (d, J = 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 146.08,
141.32, 141.04, 135.61, 134.22, 131.84, 129.09, 127.40, 127.16,
126.20, 125.95, 125.65, 124.56, 124.03, 123.39, 120.36, 119.90,
109.99, 40.43, 22.79; HRMS (ESI) m/z calcd for C30H23N
[M+H]+ 398.1903, found 398.1903.
4.6. 1-(1-(4-fluorophenyl)ethyl)naphthalene [2g]
1
Light yellow solid, 70% yield, M.p. 92.1-92.5 °C; H NMR
(400 MHz, CDCl3) δ 8.04–7.97 (m, 1H), 7.90–7.73 (m, 2H), 7.44
(dt, J = 8.8 Hz, 4H), 7.23–7.14 (m, 2H), 6.95 (t, J = 8.8 Hz, 2H),
4.91 (q, J = 7.2 Hz, 1H), 1.76 (d, J = 7.2 Hz, 3H); 13C NMR (101
MHz, CDCl3) δ 161.35, 141.43, 129.14, 129.06, 128.98, 125.53,
124.37, 123.98, 115.41, 115.20, 40.00, 22.79; HRMS (ESI) m/z
calcd for C18H15F [M+H]+ 251.1230, found 251.1226.
4.13. 3-(1-(naphthalen-1-yl)ethyl)-9-phenyl-9H-carbazole [2n]
1
Gray solid, 71% yield, M.p.120.1-120.6 °C; H NMR (400
4.7. 1-(1-(m-tolyl)ethyl)naphthalene [2h]
MHz, CDCl3) δ 8.20 (d, J = 9.8 Hz, 1H), 8.14–8.03 (m, 2H),
7.91–7.85 (m, 1H), 7.79 (dd, J = 7.2, 2.1 Hz, 1H), 7.56 (m, J =
14.4, 9.5, 7.0 Hz, 6H), 7.50–7.43 (m, 3H), 7.42–7.37 (m, 2H),
7.31 (dd, J = 4.2, 1.1 Hz, 2H), 7.28 (s, 2H), 5.17 (q, J = 7.2 Hz,
1H), 1.92 (d, J = 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ
142.41, 141.25, 139.58, 138.65, 137.95, 134.18, 131.91, 129.92,
128.90, 127.40, 127.08, 126.20, 125.95, 125.63, 125.42, 124.53,
124.28, 123.50, 120.41, 119.86, 119.02, 109.87, 40.79, 23.32;
HRMS (ESI) m/z calcd for C30H23N [M+H]+ 398.1903, found
398.1903.
1
Colourless liquid, 70% yield; H NMR (400 MHz, CDCl3) δ
8.05 (dd, J = 6.4, 3.5 Hz, 1H), 7.86–7.70 (m, 2H), 7.49–7.36 (m,
4H), 7.14 (t, J = 7.6 Hz, 1H), 7.07–6.93 (m, 3H), 4.88 (q, J = 7.2
Hz, 1H), 2.27 (s, 3H), 1.74 (d, J = 7.2 Hz, 3H); 13C NMR (101
MHz, CDCl3) δ 146.71, 141.83, 138.06, 134.11, 131.88, 128.88,
128.48, 126.97, 125.98, 125.50, 124.81, 124.45, 124.12, 40.63,
22.76, 21.65; HRMS (ESI) m/z calcd for C19H18 [M+H]+
247.1481, found 247.1482.
4.8. 1-(1-(o-tolyl)ethyl)naphthalene [2i]
4.14. 9-(3-(1-(naphthalen-1-yl)ethyl)phenyl)-9H-carbazole [2o]
1
Colourless liquid, 65% yield; H NMR (400 MHz, CDCl3) δ
1
8.02–7.97 (m, 1H), 7.84 (dd, J = 7.6, 2.1 Hz, 1H), 7.70 (d, J = 8.4
Hz, 1H), 7.48–7.41 (m, 2H), 7.40–7.35 (m, 1H), 7.23–7.10 (m,
5H), 5.02 (q, J = 7.2 Hz, 1H), 2.26 (s, 3H), 1.69 (d, J = 7.2 Hz,
3H); 13C NMR (101 MHz, CDCl3) δ 144.54, 142.25, 135.84,
134.06, 131.70, 130.60, 129.03, 126.90, 126.86, 126.24, 126.22,
126.13, 125.65, 125.46, 124.34, 123.52, 36.98, 21.39, 19.69;
HRMS (ESI) m/z calcd for C19H18 [M+H]+ 247.1481, found
247.1479.
Colourless liquid, 84% yield; H NMR (400 MHz, CDCl3) δ
8.13–8.03 (m, 3H), 7.87 (dd, J = 6.0, 3.4 Hz, 1H), 7.76 (d, J = 7.6
Hz, 1H), 7.53–7.43 (m, 5H), 7.29 (m, 9H), 5.02 (q, J = 7.2 Hz,
1H), 1.85 (d, J = 7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ
149.01, 140.97, 140.80, 137.83, 134.26, 129.94, 129.08, 127.47,
126.74, 126.31, 126.14, 125.96, 125.64, 125.56, 124.47, 124.45,
124.10, 123.42, 120.34, 119.92, 109.88, 40.70, 22.51; HRMS
(ESI) m/z calcd for C30H23N [M+H]+ 398.1903, found 398.1902.
4.9. 3-(1-(naphthalen-1-yl)ethyl)thiophene [2j]
4.15. 4-(1-(naphthalen-1-yl)ethyl)-N,N-diphenylaniline [2p]
1
1
Colourless liquid, 41% yield; H NMR (400 MHz, CDCl3) δ
Colourless liquid, 53% yield; H NMR (400 MHz, CDCl3) δ
8.16–8.11 (m, 1H), 7.92–7.87 (m, 1H), 7.76 (d, J = 8.4 Hz, 1H),
7.52–7.42 (m, 3H), 7.33 (d, J = 6.8 Hz, 1H), 7.25 (dd, J = 5.2, 3.1
Hz, 1H), 7.02–6.99 (m, 1H), 6.92 (dd, J = 5.2 Hz, 1H), 5.01 (q, J
= 7.2 Hz, 1H), 1.80 (d, J = 7.2 Hz, 3H); 13C NMR (101 MHz,
CDCl3) δ 147.32, 142.15, 134.10, 131.55, 129.01, 128.14, 127.07,
126.02, 125.72, 125.49, 124.37, 123.69, 120.40, 36.37, 22.20;
8.09 (d, J = 9.7 Hz, 1H), 7.88–7.81 (m, 1H), 7.74 (d, J = 7.9 Hz,
1H), 7.52–7.38 (m, 4H), 7.24–7.17 (m, 4H), 7.02 (m, 10H), 4.88
(q, J = 7.2 Hz, 1H), 1.75 (d, J = 7.2 Hz, 3H); 13C NMR (101 MHz,
CDCl3) δ 145.90, 141.62, 141.09, 138.99, 134.15, 128.95, 128.82,
128.17, 127.30, 127.19, 127.16, 127.12, 126.06, 125.62, 125.50,
124.50, 124.11, 40.38, 22.69; HRMS (ESI) m/z calcd for
C30H25N [M+H]+ 400.2059, found 400.2056.