Jonnada Krishna et al.
FULL PAPERS
(
(
1
C ), 85.4 (C ), 61.3 (CH ), 61.1 (CH ), 56.0 (CH ); IR
6.86 (d, 1H, J=8.8 Hz), 6.69 (d, 1H, J=8.8 Hz), 6.62 (s,
q
q
3
À1
3
3
MIR-ATR, 4000–600 cm ): n =2924, 2851, 2205, 1591,
1H), 6.45 (d, 1H, J=8.8 Hz), 3.89 (s, 3H), 3.88 (s, 3H), 3.87
max
À1
13
497, 1464, 1411, 1288, 1263, 1095, 1039, 1016, 900, 802 cm ;
(s, 9H), 3.80 (s, 3H); C NMR (CDCl , 100 MHz): d=153.0
3
+
HR-MS
(ESI ):
m/z=291.0988,
calculated
for
(C ), 152.7 (C ), 152.0 (C ), 151.5 (C ), 142.4 (C ), 142.1
q
q
q
q
q
+
+
[C H NaO ] [M+Na] : 291.0992.
(C ), 125.1 (C ), 124.4 (CH), 124.2 (C ), 124.1 (CH), 122.0
1
7
16
3
q
q
q
[(Z)-2-Phenylvinyl]benzene (5a):GP-3 was carried out
(CH), 120.5 (CH), 107.8 (CH), 107.0 (CH), 61.3 (CH ), 61.0
3
with aryl bromide 1b and the product 5a was furnished as
(CH ), 60.9 (CH ), 60.8 (CH ), 56.0 (CH ), 55.8 (CH ); IR
3
3
3
3
3
À1
a colorless oil; yield: 34 mg (75%); TLC control: R (1b)=
(MIR-ATR, 4000–600 cm ): n =2935, 2838, 1595, 1496,
max
+
f
À1
0
.80, R (5a)=0.80 (petroleum ether, UV detection);
1462, 1413, 1290, 1233, 1095, 905, 799 cm ; HR-MS (ESI ):
+ +
f
1
H NMR (CDCl , 400 MHz): d=7.30–7.10 (m, 10H), 6.58 (s,
2
m/z=383.1460, calculated for [C H NaO ] [M+Na] :
20 24 6
3
13
H); C NMR (CDCl , 100 MHz): d=137.2 (2C ), 130.2
383.1465.
3
q
(
(
1
2CH), 128.8 (4CH), 128.2 (4CH), 127.0 (2CH); IR
1-Methyl-5-[(Z)-2-(1-methyl-1H-indol-5-yl)vinyl]-1H-
indole (5f): GP-3 was carried out with aryl halide 1l and the
product 5f was furnished as a pale yellow viscous liquid;
yield: 53 mg (74%); TLC control: R (1l)=0.70, R (5f)=0.40
À1
MIR-ATR, 4000–600 cm ): n =2984, 1447, 1372, 1233,
max
À1
+
043, 938 cm ; HR-MS (ESI ): m/z=180.0934, calculated
+
+
for [C H ] [M] : 180.0934.
14
12
f
f
1
-Methoxy-4-[(Z)-2-(4-methoxyphenyl)vinyl]benzene
5b): GP-3 was carried out with aryl bromide 1j and the
product 5b was furnished as a yellow viscous liquid; yield:
0 mg (68%); TLC control: R (1j)=0.65, R (5b)=0.45 (pe-
(petroleum ether/ethyl acetate 70:30, UV detection);
1
(
H NMR (CDCl , 400 MHz): d=7.62 (s, 2H), 7.23 (dd, 2H,
3
J=8.8 and 1.5 Hz), 7.13 (d, 2H, J=8.8 Hz), 7.00 (d, 2H, J=
2.9 Hz), 6.68 (s, 2H), 6.40 (d, 2H, J=3.0 Hz), 3.75 (s, 6H);
4
f
f
1
13
troleum ether/ethyl acetate 95:5, UV detection); H NMR
CDCl , 400 MHz): d=7.22 (d, 4H, J=7.8 Hz), 6.78 (d, 4H,
J=7.8 Hz), 6.46 (s, 2H), 3.80 (s, 6H); C NMR (CDCl3,
00 MHz): d=158.4 (2C ), 130.0 (4CH), 129.9 (2C ),
28.3 (2CH), 113.5 (4CH), 55.2 (2CH ); IR (MIR-
ATR, 4000–600 cm ): n =3004, 2924, 2836, 1607, 1510,
463, 1250, 1176, 1032, 722 cm ; HR-MS (ESI ): m/z=
41.1224, calculated for [C H O ] [M+H] : 241.1223.
C NMR (CDCl , 100 MHz): d=135.8 (2C ), 129.2 (2
3
q
(
CH), 129.1 (2C ), 128.9 (2CH), 128.3 (2C ), 123.1 (2
3
q
q
13
CH), 121.3 (2CH), 108.7 (2CH), 101.1 (2CH), 32.8 (2
À1
1
1
CH ); IR (MIR-ATR, 4000–600 cm ): n =2928, 1650,
q
q
3
max
À1
+
1493, 1388, 1253, 1097, 661 cm ; HR-MS (ESI ): m/z=
+ +
287.1545, calculated for [C H N ] [M+H] : 287.1543.
20 19 2
3
À1
max
À1
+
1
2
[(E)-2-Phenylvinyl]benzene (6a): GP-4 was carried out
with aryl iodide 2b and the product 6a was furnished as
a white solid; yield: 34 mg (76%); mp 124–1268C; TLC con-
trol: R (2b)=0.80, R (6a)=0.80 (petroleum ether, UV detec-
+
+
16
17
2
1-Methoxy-3-[(Z)-2-(3-methoxyphenyl)vinyl]benzene
[28]
(
5c): GP-3 was carried out with aryl bromide 1i and the
product 5c was furnished as a colorless oil; yield: 48 mg
80%); TLC control: R (1i)=0.70, R (5c)=0.50 (petroleum
f
f
1
tion); H NMR (CDCl , 400 MHz): d=7.57 (d, 4H, J=
3
(
7.8 Hz), 7.42 (dd, 4H, J=7.8 and 7.3 Hz), 7.32 (dd, 2H, J=
f
f
1
13
ether/ethyl acetate 95:5, UV detection); H NMR (CDCl ,
7.8 and 7.3 Hz), 7.17 (s, 2H); C NMR (CDCl , 100 MHz):
3
3
4
2
6
1
1
1
00 MHz): d=7.16 (dd, 2H, J=7.8 and 7.8 Hz), 6.86 (ddd,
H, J=7.8 and 2.4 Hz), 6.81 (dd, 2H, J=2.5 and 2.5 Hz),
.76 (dd, 1H, J=2.4 and 1.0 Hz), 6.74 (dd, 1H, J=2.4 and
d=137.3 (2C ), 128.6 (2CH), 128.6 (4CH), 127.6 (2
q
À1
CH), 126.5 (4CH); IR (MIR-ATR, 4000–600 cm ): n
=
max
À1
2921, 2851, 1495, 1452, 1153, 1071, 965, 760, 691 cm ; HR-
13
+
+
+
.0 Hz), 6.59 (s, 2H), 3.67 (s, 6H); C NMR (CDCl3,
MS (ESI ): m/z=180.0937, calculated for [C H ] [M] :
14
12
00 MHz): d=159.3 (2C ), 138.5 (2C ), 130.3 (2CH),
180.0934.
q
q
[
29]
29.2 (2CH), 121.5 (2CH), 113.8 (2CH), 113.3 (2
1-[(E)-2-(1-Naphthyl)vinyl]naphthalene (6b): GP-4 was
carried out with aryl bromide 1c and the product 6b was fur-
nished as a pale yellow solid; yield: 52 mg (75%); mp 162–
1638C; TLC control: R (1c)=0.80, R (6b)=0.70 (petroleum
À1
CH), 55.0 (2CH ); IR (MIR-ATR, 4000–600 cm ): n
=
3
max
3
1
2
003, 2923, 2852, 1596, 1575, 1485, 1462, 1431, 1256, 1159,
À1
+
041, 869, 805, 777.1, 684 cm ; HR-MS (ESI ): m/z=
f
f
+
+
1
41.1224, calculated for [C H O ] [M+H] : 241.1223.
ether, UV detection); H NMR (CDCl , 400 MHz): d=8.30
16
17
2
3
4
-[(Z)-2-(3,4-Dimethoxyphenyl)vinyl]-1,2-dimethoxyben-
(dd, 2H, J=7.3 and 2.4 Hz), 8.05–7.80 (m, 8H), 7.65–7.50
1
3
zene (5d): GP-3 was carried out with aryl iodide 2i and the
(m, 6H); C NMR (CDCl , 100 MHz): d=135.3 (2C ),
3
q
product 5d was furnished as a yellow viscous liquid; yield:
133.7 (2C ), 131.4 (2C ), 128.9 (2CH), 128.6 (2 CH),
q
q
5
1 mg (68%); TLC control: R (2i)=0.80, R (5d)=0.50 (pe-
128.2 (2CH), 126.1 (2CH), 125.9 (2CH), 125.7 (2
f
f
1
troleum ether/ethyl acetate 70:30, UV detection); H NMR
CH), 123.9 (2CH), 123.8 (2CH); IR (MIR-ATR, 4000–
À1
(CDCl , 400 MHz): d=6.84 (dd, 2H, J=8.3 and 2.0 Hz),
600 cm ): n =3055, 2923, 1590, 1508, 1435, 1383, 1343,
3
max
À1
6
6
.83 (s, 2H), 6.75 (d, 2H, J=8.3 Hz), 6.46 (s, 2H), 3.85 (s,
1262, 1211, 1151, 1151, 1013, 917, 776, 727 cm ; HR-MS
(ESI ): m/z=281.1326, calculated for [C H ] [M+H] :
13
+
+
+
H), 3.67 (s, 6H); C NMR (CDCl , 100 MHz): d=148.3
3
22 17
(
2C ), 148.0 (2C ), 130.1 (2C ), 128.7 (2CH), 121.7
281.1325.
q
q
q
(
2CH), 111.7 (2CH), 110.8 (2CH), 55.8 (2CH ), 55.6
1-Methoxy-3-[(E)-2-(3-methoxyphenyl)vinyl]benzene
(6c): GP-4 was carried out with aryl bromide 1i and the
3
À1
[30]
(2CH ); IR (MIR-ATR, 4000–600 cm ): n =3000, 2933,
3
max
2
8
835, 1604, 1513, 1460, 1405, 1329, 1245, 1171, 1137, 1025,
product 6c was furnished as a white solid; yield: 48 mg
(80%); mp 160–1618C; TLC control: R (1i)=0.65, R (6c)=
À1
+
10, 762 cm ; HR-MS (ESI ): m/z=323.1253, calculated for
f
f
+
+
[C H NaO ] [M+Na] : 323.1254.
0.45 (petroleum ether/ethyl acetate 95:5, UV detection);
1
8
20
4
1
1,2,3-Trimethoxy-4-[(Z)-2-(2,3,4-trimethoxyphenyl)vinyl]-
H NMR (CDCl , 400 MHz): d=7.27 (dd, 2H, J=7.8 and
3
benzene (5e): GP-3 was carried out with aryl iodide 2j and
the product 5e was furnished as a viscous liquid; yield:
7.8 Hz), 7.11 (d, 2H, J=7.8 Hz), 7.07 (s, 2H), 7.04 (dd, 2H,
J=2.4 and 1.4 Hz), 6.81 (ddd, 2H, J=2.4 and 1.0 Hz), 3.84
1
3
6
2 mg (70%); TLC control: R (2j)=0.70, R (5e)=0.40 (pe-
(s, 6H); C NMR (CDCl , 100 MHz): d=159.9 (2C ),
f
f
3
q
1
troleum ether/ethyl acetate 70:30, UV detection); H NMR
138.7 (2C ), 129.6 (2CH), 128.9 (2CH), 119.3 (2CH),
q
(
CDCl , 400 MHz): d=7.33 (d, 1H, J=8.8 Hz), 7.23 (s, 1H),
113.3 (2CH), 111.7 (2CH), 55.2 (2CH ); IR (MIR-
3
3
3
608
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2015, 357, 3597 – 3610