C. Xu, Z. He, H. Yang et al.
Tetrahedron xxx (xxxx) xxx
CDCl3)
d
¼ 7.53e7.40 (m, 2H), 7.27e7.10 (m, 6H), 7.05e6.95 (m, 1H),
(2-(4-fluorophenyl)-2-(4-methoxy-2,6-dimethylphenyl)ethyl)(-
phenyl)selane (4fda). Colorless oily liquid, 56% yield, 115 mg; 1H
6.15e6.07 (m, 2H), 4.92 (dd, J ¼ 9.7, 7.0, 1H), 3.93e3.87 (m, 1H),
3.84e3.80 (m, 3H), 3.78e3.66 (m, 7H), 2.32e2.29 (m, 3H); 13C NMR
NMR (400 MHz, CDCl3)
d
¼ 7.40e7.31 (m, 2H), 7.18e7.10 (m, 5H),
(75 MHz, Chloroform-d)
d
¼ 159.82, 159.21, 144.12, 137.12, 132.49,
6.88e6.79 (m, 2H), 6.55e6.49 (m, 1H), 6.43 (s, 1H), 4.49 (t, J ¼ 7.5,
128.65, 127.62, 126.45, 126.24, 124.83, 112.36, 91.14, 55.60, 55.14,
40.13, 31.60, 21.53; HRMS (ESI): calculated for C24H27O3Se [M þ
H]þ ¼ 443.1120, found 443.1120.
1H), 3.75 (dd, J ¼ 11.8, 8.5, 1H), 3.69e3.61 (m, 1H), 3.55 (s, 3H), 2.20
(s, 3H), 2.09 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 160.99 (d,
J ¼ 243.8), 157.97, 139.15 (d, J ¼ 2.9), 137.40, 137.26, 132.61, 130.78,
129.19, 129.09, 128.82, 126.54, 124.04, 114.63, 114.35, 110.56, 54.96,
43.51, 31.54, 21.24, 20.59; HRMS (ESI): calculated for C23H23FNaOSe
[M þ Na]þ ¼ 437.0788, found 437.0791.
(2-(4-(tert-butyl)phenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(-
phenyl)selane (4caa). Yellow viscous liquid, 51% yield, 123 mg; 1H
NMR (400 MHz, Chloroform-d)
d
¼ 7.47e7.28 (m, 2H), 7.23e7.01
(m, 8H), 6.01 (s, 2H), 4.82 (dd, J ¼ 10.0, 6.7, 1H), 3.85 (dd, J ¼ 11.4,
(2-(4-chlorophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(phenyl)
selane (4gaa). [20] Yellow viscous liquid, 87% yield, 200 mg; 1H
10.0, 1H), 3.68 (s, 3H), 3.63e3.53 (m, 4H), 1.19 (s, 9H); 13C NMR
(101 MHz, Chloroform-d)
d
¼ 159.87, 159.32, 148.32, 141.28, 132.62,
NMR (400 MHz, CDCl3)
6.01 (s, 2H), 4.84e4.75 (m, 1H), 3.70 (d, J ¼ 4.6, 4H), 3.64e3.58 (m,
7H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 7.38e7.32 (m, 2H), 7.18e7.08 (m, 7H),
131.52, 128.71, 127.50, 126.31, 124.77, 112.40, 91.20, 55.68, 55.22,
39.98, 34.31, 31.94, 31.43; HRMS (ESI): calculated for C27H32O3SeNa
[M þ Na]þ ¼ 507.1411, found 507.1411.
d
¼ 160.04, 158.99, 142.68,
132.61, 131.20, 131.07, 129.27, 128.71, 127.77, 126.42, 112.01, 91.08,
(2-([1,10-biphenyl]-4-yl)-2-(2,4,6-trimethoxyphenyl)ethyl)(-
phenyl)selane (4daa). Yellow viscous liquid, 47% yield, 118 mg; 1H
55.56, 55.16, 39.62, 31.12. HRMS (ESI): calculated for C23H23ClO3
-
SeNa [M þ Na]þ ¼ 485.0390, found 485.0394.
(2-(4-chlorophenyl)-2-(2,4,5-trimethoxyphenyl)ethyl)(phenyl)
selane (4gba). Yellow viscous liquid, 76% yield, 175 mg; 1H NMR
NMR (400 MHz, Chloroform-d)
d
¼ 7.47e7.42 (m, 2H), 7.39e7.33
(m, 4H), 7.32e7.26 (m, 4H), 7.20e7.15 (m, 1H), 7.12e7.05 (m, 3H),
6.00 (s, 2H), 4.88 (dd, J ¼ 9.5, 7.1, 1H), 3.82 (dd, J ¼ 11.5, 9.5, 1H),
3.70e3.64 (m, 4H), 3.59 (s,3H); 13C NMR (75 MHz, Chloroform-d)
(300 MHz, CDCl3)
d
¼ 7.52e7.45 (m, 2H), 7.29e7.19 (m, 7H), 6.68 (s,
1H), 6.51 (s, 1H), 4.65 (t, J ¼ 8.0, 1H), 3.88 (s, 3H), 3.76 (d, J ¼ 16.3,
6H), 3.63e3.46 (m, 2H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 160.09, 159.31, 143.55, 141.29, 138.61, 132.71, 131.47, 128.85,
d
¼ 151.16, 148.43, 142.82, 141.83, 132.57, 131.83, 130.64, 129.24,
128.75, 128.42, 127.05, 126.98, 126.66, 126.48, 112.36, 91.28, 55.75,
55.29, 40.11, 31.62; HRMS (ESI): calculated for C29H28O3SeNa [M þ
Na]þ ¼ 527.1091, found 527.1096.
128.78, 128.21, 126.63, 122.86, 112.45, 97.78, 56.69, 56.13, 55.92,
43.75, 32.35; HRMS (ESI): calculated for C23H23ClO3SeNa [M þ
Na]þ ¼ 485.0388, found 485.0394.
phenyl(2-(4-(trifluoromethyl)phenyl)-2-(2,4,6-
(2-(4-chlorophenyl)-2-(2,3,4-trimethoxy-6-methylphenyl)eth-
yl)(phenyl)selane (4gca). White viscous liquid, 70% yield, 166 mg;
trimethoxyphenyl)ethyl)selane (4eaa). Yellow viscous liquid, 70%
yield, 173 mg; 1H NMR (400 MHz, CDCl3)
d
¼ 7.54e7.40 (m, 6H),
1H NMR (400 MHz, CDCl3)
d
¼ 7.43e7.34 (m, 2H), 7.18e7.10 (m, 7H),
7.28e7.21 (m, 3H), 6.12 (s, 2H), 4.99 (t, J ¼ 8.2, 1H), 3.90e3.80 (m,
4H), 3.79e3.70 (m, 7H); 13C NMR (75 MHz, Chloroform-d)
6.37 (s, 1H), 4.43 (s, 1H), 3.77e3.67 (m, 7H), 3.60 (dd, J ¼ 11.8, 8.1,
1H), 3.29 (d, J ¼ 18.2, 3H), 2.12 (s, 3H); 13C NMR (75 MHz,
d
¼ 160.18, 158.95, 148.31, 132.66, 130.86, 128.71, 128.16, 127.46,
Chloroform-d)
d
¼ 152.48, 152.06, 142.34, 140.62, 132.78, 131.74,
126.49, 124.58, 124.53, 111.58, 90.99, 55.45, 55.07, 40.07, 30.74;
HRMS (ESI): calculated for C24H24F3O3Se [M þ H]þ ¼ 497.0841,
found 497.0838.
131.48, 130.76, 129.00, 128.05, 127.73, 126.84, 124.24, 109.18, 60.49,
60.00, 55.76, 43.43, 31.16, 20.92; HRMS (ESI): calculated for
C
24H26ClO3Se [M þ H]þ ¼ 477.0735, found 477.0730.
(2-(4-fluorophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(phenyl)
selane (4faa). [20] Yellow viscous liquid, 76% yield, 169 mg; 1H NMR
(2-(4-chlorophenyl)-2-(4-methoxy-2,6-dimethylphenyl)eth-
yl)(phenyl)selane (4gda). Colorless oily liquid, 67% yield, 144 mg;
(400 MHz, CDCl3)
d
¼ 7.47e7.40 (m, 2H), 7.30e7.19 (m, 5H),
1H NMR (400 MHz, CDCl3)
d
¼ 7.49e7.42 (m, 2H), 7.28e7.18 (m, 7H),
6.94e6.84 (m, 2H), 6.09 (s, 2H), 4.93e4.83 (m, 1H), 3.85e3.77 (m,
4H), 3.73e3.65 (m, 7H); 13C NMR (75 MHz, Chloroform-d)
6.62 (s, 1H), 6.52 (s, 1H), 4.58 (t, J ¼ 7.6, 1H), 3.86e3.73 (m, 2H), 3.64
(s, 3H), 2.30 (s, 3H), 2.19 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 162.50, 159.87, 159.28, 158.88, 139.77, 132.45, 131.03, 129.25,
d
¼ 158.02, 142.06, 137.48, 132.73, 131.40, 130.75, 129.16, 128.90,
129.15, 128.62, 126.29, 114.41, 114.13, 112.08, 90.96, 55.42, 54.99,
127.92, 126.67, 126.58, 124.09, 110.60, 55.07, 43.62, 31.29, 21.31,
39.44, 31.33; HRMS (ESI): calculated for
C
23H24FO3Se [M
þ
H]þ ¼ 447.0856, found 447.0870.
20.65; HRMS (ESI): calculated for
C
23H23ClOSeNa [M
þ
Na]þ ¼ 453.0493, found 453.0495.
(2-(4-fluorophenyl)-2-(2,4,5-trimethoxyphenyl)ethyl)(phenyl)
selane (4fba). Yellow viscous liquid, 67% yield, 149 mg; 1H NMR
(2-(4-bromophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)(phenyl)
selane (4haa). [20] Yellow viscous liquid, 90% yield, 227 mg; 1H
(400 MHz, CDCl3)
d
¼ 7.47e7.32 (m, 2H), 7.15 (dddd, J ¼ 11.5, 8.4,
NMR (400 MHz, CDCl3)
d
¼ 7.42e7.30 (m, 2H), 7.30e7.20 (m, 2H),
5.6, 2.6, 5H), 6.94e6.83 (m, 2H), 6.56 (s, 1H), 6.41 (s, 1H), 4.55 (t,
J ¼ 8.1,1H), 3.79 (s, 3H), 3.67 (d, J ¼ 13.2, 6H), 3.52e3.36 (m, 2H); 13
C
7.14 (ddt, J ¼ 11.7, 9.5, 4.8, 5H), 6.00 (s, 2H), 4.84e4.71 (m, 1H),
3.75e3.68 (m, 4H), 3.66e3.57 (m, 7H); 13C NMR (75 MHz, CDCl3)
NMR (75 MHz, Chloroform-d)
d
¼ 162.94, 159.70, 151.20, 148.38,
d
¼ 160.03, 158.96, 143.20, 132.60, 131.03, 130.69, 129.68, 128.69,
142.84, 139.01, 132.61, 130.83, 129.38 (d, J ¼ 7.8), 128.86, 126.69,
126.41, 119.31, 111.90, 91.06, 55.53, 55.14, 39.67, 31.01; HRMS (ESI):
calculated for C23H24BrO3Se [M þ H]þ ¼ 507.0074, found 507.0069.
(2-(4-bromophenyl)-2-(2,4,5-trimethoxyphenyl)ethyl)(phenyl)
selane (4hba). Yellow viscous liquid, 85% yield, 215 mg; 1H NMR
123.24, 114.99 (d, J ¼ 21.1), 112.39, 97.79, 56.72, 56.26, 55.99, 43.65,
32.72; HRMS (ESI): calculated for
C
23H23FO3SeNa [M
þ
Na]þ ¼ 469.0673, found 469.0689.
(2-(4-fluorophenyl)-2-(2,3,4-trimethoxy-6-methylphenyl)eth-
yl)(phenyl)selane (4fca). White viscous liquid, 60% yield, 138 mg;
(400 MHz, CDCl3)
d
¼ 7.44e7.26 (m, 4H), 7.19e7.14 (m, 3H),
1H NMR (400 MHz, Chloroform-d)
d
¼ 7.42e7.33 (m, 2H), 7.15 (qd,
7.08e7.00 (m, 2H), 6.56 (s, 1H), 6.40 (s, 1H), 4.52 (t, J ¼ 8.1, 1H), 3.79
(s, 3H), 3.66 (d, J ¼ 18.5, 6H), 3.51e3.34 (m, 2H); 13C NMR (75 MHz,
J ¼ 5.1, 4.5, 2.5, 5H), 6.90e6.85 (m, 2H), 6.37 (s, 1H), 4.45 (t, J ¼ 6.9,
1H), 3.76e3.73 (m, 4H), 3.69 (s, 3H), 3.62 (dd, J ¼ 11.8, 8.2, 1H), 3.31
Chloroform-d)
d
¼ 151.23, 148.50, 142.87, 142.42, 132.68, 131.27,
(s, 3H), 2.13 (s, 3H); 13C NMR (75 MHz, Chloroform-d)
d
¼ 161.02 (d,
130.71, 129.72, 128.88, 126.75, 122.82, 120.09, 112.41, 97.77, 56.78,
56.24, 56.02, 43.90, 32.37; HRMS (ESI): calculated for C23H23BrO3
J ¼ 244.2), 152.45, 151.93, 140.57, 139.41, 132.65, 131.68, 130.79,
128.95, 128.29 (d, J ¼ 7.5), 127.92, 126.74, 114.66 (d, J ¼ 21.0), 109.10,
60.44, 59.94, 55.69, 43.28, 31.36, 20.90; HRMS (ESI): calculated for
-
SeNa [M þ Na]þ ¼ 528.9870, found 528.9888.
(2-(4-bromophenyl)-2-(2,3,4-trimethoxy-6-methylphenyl)eth-
yl)(phenyl)selane (4hca). White viscous liquid, 74% yield, 192 mg;
C
24H25FO3SeNa [M þ Na]þ ¼ 483.0858, found 483.0845.
1H NMR (400 MHz, CDCl3)
d
¼ 7.38e7.33 (m, 2H), 7.28 (d, J ¼ 8.5,
6