10.1002/adsc.201700676
Advanced Synthesis & Catalysis
33.1; HRMS (EI) for C14H14SeO (M+): calcd.
278.0210, found 278.0211.
(dd, J = 8.3, 5.5 Hz, 2H), 6.89 (t, J = 8.6 Hz, 2H),
4.04 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 161.7 (d,
JC, F = 245.4 Hz), 134.4 (d, JC,F = 3.2 Hz), 133.8,
130.3(d, JC,F = 8.1 Hz), 129.9, 129.0, 127.4, 115.2 (d,
JC,F = 21.5 Hz), 31.3; HRMS (EI) for C13H11SeF
(M+): calcd. 266.0010, found 266.0009.
Benzyl(3,5-dimethylphenyl)selane (3c): Yellow
oil; yield 99 mg, 72%; 1H NMR (400 MHz, CDCl3) δ
7.36-7.28 (m, 5H), 7.16 (s, 2H), 6.96 (s, 1H), 4.18 (s,
13
2H), 2.34 (s, 6H); C NMR (100 MHz, CDCl3) δ
138.7, 138.5, 131.0, 130.1, 128.9 (2C), 128.4, 126.8,
32.0, 21.1; HRMS (EI) for C15H16Se (M+): calcd.
276.0417, found 276.0416.
(3-Chlorobenzyl)(phenyl)selane (3k):[23] Yellow
oil; yield 124 mg, 88%; 1H NMR (400 MHz, CDCl3)
δ 7.47-7.37 (m, 2H), 7.25-7.19 (m, 3H), 7.16-7.08 (m,
3H), 7.05-6.97 (m, 1H), 3.99 (s, 2H); 13C NMR (100
MHz, CDCl3) δ 140.7, 133.9 (2C), 129.6 (2C), 128.9
(2C), 127.6, 126.9 (2C), 31.5; HRMS (EI) for
C13H11SeCl (M+): calcd. 281.9715, found 281.9713.
(3-Bromobenzyl)(phenyl)selane (3l):[22] Yellow
Benzyl(4-(trifluoromethyl)phenyl)selane (3d):[20]
1
Yellow solid; mp 63-65 oC; yield 131 mg, 83%; H
NMR (400 MHz, CDCl3) 1H NMR (400 MHz,
CDCl3) δ 7.48 (dd, J = 19.6, 8.4 Hz,4H), 7.28 – 7.21
(m, 5H), 4.17 (s, 2H).; 13C NMR (100 MHz, CDCl3) δ
1
oil; yield 139 mg, 85%; H NMR (400 MHz, CDCl3)
137.6, 135.9 (q, JC,F = 1.5 Hz), 132.4, 129.5(q, JC,F
=
δ 7.40 (d, J = 6.1 Hz, 2H), 7.30-7.18 (m, 5H), 7.05 (d,
J = 3.4 Hz, 2H), 3.97 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 140.5, 135.0, 134.1, 132.7, 129.9, 129.3,
128.9, 127.8, 127.4, 127.2, 33.2; HRMS (EI) for
C13H11SeBr (M+): calcd. 325.9209, found 325.9209.
(2-Bromobenzyl)(phenyl)selane (3m):[24] Yellow
oil; yield 134 mg, 82%; 1H NMR (400 MHz, CDCl3)
δ 7.52 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 7.7, 1.4 Hz,
2H), 7.27-7.19 (m, 3H), 7.12-7.07 (m, 1H), 7.02 (ddd,
J = 8.9, 5.6, 1.7 Hz, 2H), 4.17 (s, 2H); 13C NMR (100
MHz, CDCl3) δ 138.3, 134.4, 133.0, 130.6, 129.8,
128.9, 128.4, 127.6, 127.2, 124.3, 32.9; HRMS (EI)
for C13H11SeBr (M+): calcd. 325.9209, found
325.9208.
26.7 Hz) 128.9, 128.6, 127.2, 126.6(q, JC,F = 270.7
Hz),125.6 (q, JC,F = 3.8 Hz), 31.8; HRMS (EI) for
C14H11SeF3 (M+): calcd. 315.9978, found 315.9980.
2-(Benzylselanyl)thiophene (3e): Yellow oil;
1
yield 95 mg, 75%; H NMR (400 MHz, CDCl3) δ
7.44 (d, J = 5.3 Hz, 1H), 7.34-7.27 (m, 3H), 7.20 (d, J
= 6.8 Hz, 2H), 7.10-7.06 (m, 1H), 7.03-6.98 (m, 1H),
4.08 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 138.5,
136.3, 131.2, 128.8, 128.4, 127.9, 126.9, 123.5, 35.5;
HRMS (EI) for C11H10SeS (M+): calcd. 253.9668,
found 253.9667.
(3-Methylbenzyl)(phenyl)selane (3f):[21] Yellow
oil; yield 102 mg, 78%; 1H NMR (400 MHz, CDCl3)
δ 7.44-7.37 (m, 2H), 7.22-7.16 (m, 3H), 7.08 (d, J =
7.4 Hz, 1H), 6.96 (d, J = 7.2 Hz, 3H), 4.03 (s, 2H),
2.24 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 138.4,
138.0, 133.4, 130.6, 129.6 128.9, 128.3, 127.6, 127.2,
125.8, 32.2, 21.3; HRMS (EI) for C14H14Se (M+):
calcd. 262.0261, found 262.0262.
2-((Phenylselanyl)methyl)thiophene
(3n):[25]
Yellow oil; yield 100 mg, 79%; 1H NMR (400 MHz,
CDCl3) δ 7.47 (dd, J = 6.2, 2.6 Hz, 2H), 7.26-7.21 (m,
3H), 7.12 (d, J = 5.1 Hz, 1H), 6.85-6.80 (m, 1H), 6.77
(d, J = 3.1 Hz, 1H), 4.28 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 141.7, 133.7, 130.1, 129.0, 127.5, 126.7,
126.1, 124.7, 25.7; HRMS (EI) for C11H10SeS (M+):
calcd. 253.9668, found 253.9670.
(2-Methylbenzyl)(phenyl)selane (3g):[21] Yellow
1
oil; yield 102 mg, 78%; H NMR (400 MHz, CDCl3)
6-((phenylselanyl)methyl)quinoline (3o): Yellow
o
1
δ 7.45 (dd, J = 7.2, 1.9 Hz, 2H), 7.25-7.20 (m, 3H),
7.11 (d, J = 5.6 Hz, 2H), 7.02 (d, J = 7.2 Hz, 2H),
4.09 (s, 2H), 2.34 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ 136.3 (2C), 133.9, 130.5 (2C), 129.7, 128.9,
127.3 (2C), 125.9, 30.5, 19.2; HRMS (EI) for
C14H14Se (M+): calcd. 262.0261, found 262.0260.
(4-Chlorobenzyl)(phenyl)selane (3h):[6c] White
solid; mp 53-55 oC(lit. 52-54 oC); yield 127 mg, 90%;
1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 2H),
7.25-7.14 (m, 5H), 7.06 (d, J = 8.4 Hz, 2H), 4.01 (s,
2H);13C NMR (100 MHz, CDCl3) δ 137.3, 133.8,
132.5, 130.0, 129.8, 129.0, 128.4, 127.5, 31.4; HRMS
(EI) for C13H11SeCl (M+): calcd. 281.9714, found
281.9710.
solid; mp 72-74 C; yield 135 mg, 90%; H NMR
(400 MHz, CDCl3) δ 8.78 (dt, J = 4.0, 1.8 Hz, 1H),
7.97 (d, J = 8.7 Hz, 1H), 7.84 (dd, J = 6.3, 2.0 Hz,
1H), 7.53 (dt, J = 8.7, 1.9 Hz, 1H), 7.42-7.31 (m, 3H),
7.24-7.08 (m, 4H), 4.14 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 149.8, 147.0, 136.7, 135.2, 133.6, 130.5,
129.6, 129.3, 128.7, 127.6, 127.2, 126.5, 120.9, 31.8;
HRMS (EI) for C16H13Se N (M+): calcd. 299.0213,
found 299.0213.
(Naphthalen-2-ylmethyl)(phenyl)selane
(3p):
1
Yellow solid; mp 33-35 oC; yield 136 mg, 91%; H
NMR (400 MHz, CDCl3) δ 7.66 (ddd, J = 21.9, 9.0,
5.2 Hz, 3H), 7.46 (s, 1H), 7.43-7.30 (m, 5H), 7.21-
7.09 (m, 3H), 4.16 (s, 2H); 13C NMR (100 MHz,
CDCl3) δ 135.9, 133.5, 133.2, 132.3, 130.3, 128.9,
128.1, 127.5 (2C), 127.2, 127.1 (2C), 126.0, 125.6,
32.5; HRMS (EI) for C17H14Se (M+): calcd. 298.0261,
found 298.0262.
(4-Bromobenzyl)(phenyl)selane (3i):[6c] White
solid; mp 55-57 oC(lit. 56-58 oC); yield 140 mg, 86%;
1H NMR (400 MHz, CDCl3) δ 7.45-7.38 (m, 2H),
7.35-7.29 (m, 2H), 7.25-7.18 (m, 3H), 7.00 (d, J = 8.4
Hz, 2H), 3.99 (s, 2H); 13C NMR (100 MHz, CDCl3) δ
137.7, 133.7, 131.3, 130.4, 129.7, 129.0, 127.4, 120.5,
31.4; HRMS (EI) for C13H11SeBr (M+): calcd.
325.9209, found 325.9208.
Benzhydryl(phenyl)selane (3q): Yellow oil; yield
143 mg, 88%; 1H NMR (400 MHz, CDCl3) δ 7.57 (dd,
J = 25.2, 7.0 Hz, 6H), 7.43 (t, J = 7.5 Hz, 4H), 7.32
(ddd, J = 16.9, 13.7, 6.8 Hz, 5H), 5.86 (d, J = 4.2 Hz,
(4-Fluorobenzyl)(phenyl)selane (3j):[22] Yellow
oil; yield 109 mg, 82%; 1H NMR (400 MHz, CDCl3)
δ 7.47-7.37 (m, 2H), 7.22 (q, J = 3.9 Hz, 3H), 7.11
13
1H); C NMR (100 MHz, CDCl3) δ 141.2, 133.9,
130.9, 128.7 (2C), 128.3, 127.4, 126.9, 52.7; HRMS
7
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