Please do not adjust margins
New Journal of Chemistry
Page 4 of 7
ARTICLE
Journal Name
1
2
3
4
5
6
7
8
9
mmol, 0.58 mL) under argon atmosphere at room temperature, (E)-2-(4-bromostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2g)
DOI: 10.1039/D0NJ02612C
reaction mixture was brought to 110 °C and stirred for 6 h. After According to general procedure, compound 2g was prepared in 76%
this time (1H NMR analysis), reaction mixture was cooled to room yield (0.76 mmol, 236 mg) as yellow solid. 1H NMR (400 MHz, CDCl3)
temperature. Then, after adding the internal standard (1,3,5- δ 7.46 (d, J = 8.4 Hz, 2H), 7.36 – 7.29 (m, 3H), 6.15 (d, J = 18.5, 1H),
trimethoxybenzene, 0.33 mmol, 5.55 mg), NMR yields are 1.31 (s, 12H, CH3, Bpin), 13C NMR (100 MHz, CDCl3) δ 148.07,
calculated.
136.38, 131.75, 128.51, 122.90, 83.48, 24.81 11B NMR (128 MHz,
CDCl3) δ 29.59.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Spectroscopic data for isolated products
(E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane (2a)
According to general procedure, compound 2a was prepared in 89%
(E)-4,4,5,5-tetramethyl-2-(3-phenylprop-1-en-1-yl)-1,3,2-dioxaborol
ane (2h) According to general procedure, compound 2h was
prepared in 85% yield (0.85 mmol, 207 mg) as colorless liquid. H
1
1
NMR (400 MHz, CDCl3) δ 7.28 (t, J = 7.6 Hz, 2H), 7.19 (dd, J = 12.4,
7.2 Hz, 3H), 6.76 (dt, J = 17.9, 6.3 Hz, 1H, CH=), 5.44 (d, J = 18 Hz, 1H,
CH=), 3.48 (d, J = 5.2 Hz, 2H, CH2), 1.25 (s, 12H, CH3, Bpin). 13C NMR
(100 MHz, CDCl3) δ 152.52, 139.00, 128.93, 128.42, 126.14, 83.10,
42.26, 24.76. 11B NMR (128 MHz, CDCl3) δ 29.17.
(Z)-4,4,5,5-Tetramethyl-2-(1,2 diphenyl-1-enyl)-1,3,2-dioxaborolane
(2j) According to general procedure, compound 2j was prepared in
90% yield (0.90 mmol, 276 mg) as white solid. 1H NMR (400 MHz,
CDCl3) δ 7.35 (s, 1H), 7.28 – 7.23 (m, 2H), 7.22 – 7.13 (m, 3H), 7.13 –
7.07 (m, 3H), 7.06 – 7.01 (m, 2H), 1.30 (s, 12H, CH3, Bpin). 13C NMR
(100 MHz, CDCl3) δ 143.16, 140.42, 136.96, 129.94, 128.84, 128.23,
127.83, 127.57, 126.25, 83.78, 24.78 11B NMR (128 MHz, CDCl3) δ
29.98.
(E)-4,4,5,5-tetramethyl-2-(2-(naphthalen-1-yl)vinyl)-1,3,2-dioxaborol
ane (2k) According to general procedure, compound 2k was
prepared in 72% yield (0.72 mmol, 201mg) as yellow liquid. 1H NMR
(400 MHz, CDCl3) δ 8.30 – 8.17 (m, 2H), 7.86 (dd, J = 12.0, 8.0 Hz,
2H), 7.73 (d, J = 7.1 Hz, 1H), 7.55 – 7.45 (m, 3H), 6.27 (d, J = 18.1 Hz,
1H), 1.35 (s, 12H, CH3, Bpin). 13C NMR (100 MHz, CDCl3) δ 146.42,
135.31, 133.57, 131.06, 129.02, 128.47, 126.16, 125.78, 125.58,
124.06, 123.76, 83.41, 24.85. 11B NMR (128 MHz, CDCl3) δ 29.60.
(E)-4,4,5,5-tetramethyl-2-(2-(thiophen-2-yl)vinyl)-1,3,2-dioxaborolan
e (2l) According to general procedure, compound 2l was prepared
in 36% yield (0.36 mmol, 84 mg) as yellow liquid. 1H NMR (400 MHz,
CDCl3) δ 7.46 (d, J = 18.0 Hz, 1H), 7.24 (d, J = 5.2 Hz, 1H), 7.07 (d, J =
3.6 Hz, 1H), 6.98 (dd, J = 3.6, 2.6 Hz, 1H), 5.90 (d, J = 18.4 Hz, 1H),
1.29 (s, 12H, CH3, Bpin). 13C NMR (100 MHz, CDCl3) δ 143.90, 141.80,
127.74, 127.62, 126.31, 83.36, 24.78 11B NMR (128 MHz, CDCl3) δ
29.81. 11B NMR (128 MHz, CDCl3) δ 29.53.
yield (0.89 mmol, 205 mg) as colorless liquid. H NMR (400 MHz,
CDCl3) δ 7.51 – 7.47 (m, 2H), 7.40 (d, J = 18.5 Hz, 1H), 7.36 – 7.27
(m, 3H), 6.17 (d, J = 18.5 Hz, 1H), 1.32 (s, 12H, CH3, Bpin). 13C NMR
(100 MHz, CDCl3) δ 149.51, 137.45, 128.89, 128.56, 127.05, 83.33,
24.81. 11B NMR (128 MHz, CDCl3) δ 29.47.
(E)-4,4,5,5-tetramethyl-2-(4-methylstyryl)-1,3,2-dioxaborolane
(2b)
According to general procedure, compound 2b was prepared in 87%
yield (0.87 mmol, 213 mg) as yellow liquid. 1H NMR (400 MHz,
CDCl3) δ 7.41 – 7.34 (m, 3H), 7.14 (d, J = 7.6 Hz, 2H), 6.11 (d, J = 18.0
Hz, 1H), 2.34 (s, 3H, CH3), 1.31 (s, 12H, CH3, Bpin). 13C NMR (100
MHz, CDCl3) δ 149.47, 138.95, 134.78, 129.28, 127.01, 83.25, 24.81,
21.33. 11B NMR (128 MHz, CDCl3) δ 29.53.
(E)-4,4,5,5-tetramethyl-2-(2-methylstyryl)-1,3,2-dioxaborolane (2c)
According to general procedure, compound 2c was prepared in 85%
yield (0.85 mmol, 209 mg) as yellow liquid. 1H NMR (400 MHz,
CDCl3) δ 7.64 (d, J = 18.3 Hz, 1H), 7.57 – 7.53 (m, 1H), 7.21 – 7.17
(m, 2H), 7.16 – 7.13 (m, 1H), 6.08 (d, J = 18.3 Hz, 1H), 2.42 (s, 3H,
CH3), 1.32 (s, 12H, CH3, Bpin). 13C NMR (100 MHz, CDCl3) δ 147.12,
136.68, 136.30, 130.39, 128.57, 126.10, 125.76, 83.30, 24.82, 19.83.
11B NMR (128 MHz, CDCl3) δ 29.30.
(E)-2-(4-methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2d)
According to general procedure, compound 2d was prepared in 87%
yield (0.87 mmol, 227 mg) as yellow liquid. H NMR (400 MHz,
CDCl3) δ 7.42 (d, J = 8.8 Hz, 2H), 7.34 (d, J = 18.3 Hz, 1H), 6.85 (d, J =
8.8 Hz, 2H), 6.00 (d, J = 18.7 Hz, 1H), 3.78 (s, 3H, OCH3), 1.29 (s, 12H,
CH3, Bpin). 13C NMR (100 MHz, CDCl3) δ 160.28, 149.06, 130.37,
128.45, 113.95, 83.19, 55.23, 24.80. 11B NMR (128 MHz, CDCl3) δ
29.55.
(E)-2-(4-fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2e)
According to general procedure, compound 2e was prepared in 66%
yield (0.66 mmol, 164 mg) as white solid. 1H NMR (400 MHz, CDCl3)
δ 7.49 – 7.43 (m, 2H), 7.35 (d, J = 18.5 Hz, 1H), 7.05 – 7.00 (m, 2H),
6.07 (d, J = 18.4 Hz, 1H), 1.31 (s, 12H, CH3, Bpin). 13C NMR (100 MHz,
CDCl3) δ 163.14(d, J = 245 Hz), 148.17, 133.68 (d, J = 3.4 Hz), 128.71
(d, J = 8.3 Hz), 115.56 (d, J = 21.7 Hz), 83.40, 24.81. 11B NMR (128
MHz, CDCl3) δ 29.69, 19F NMR (376 MHz, CDCl3) δ (ppm) -112.2.
(E)-2-(4-chlorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2f)
According to general procedure, compound 2f was prepared in 79%
yield (0.79 mmol, 209 mg) as white solid. 1H NMR (400 MHz, CDCl3)
δ 7.44 – 7.34 (m, 3H), 7.32 – 7.28 (m, 2H), 6.13 (d, J = 18.5 Hz, 1H),
1.31 (s, 12H, CH3, Bpin). 13C NMR (100 MHz, CDCl3) δ 148.02,
135.95, 134.61, 128.80, 128.23, 83.47, 24.81. 11B NMR (128 MHz,
CDCl3) δ 29.69.
1
(E)-2-(4-ethynylstyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
(2m) According to general procedure, compound 2m was prepared
in 37% yield (0.37 mmol, 94mg) as white solid. 1H NMR (400 MHz,
CDCl3) δ 7.47 (s, 4H), 7.36 (d, J = 18.4 Hz, 1H), 6.18 (d, J = 18.7 Hz,
1H), 3.13 (s, 1H, CH), 1.31 (s, 12H, CH3, Bpin). 13C NMR (100 MHz,
≡
CDCl3) δ 148.38, 137.75, 132.34, 126.88, 122.37, 83.43, 78.31, 24.79
11B NMR (128 MHz, CDCl3) δ 29.47.
1,4-Bis((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benz
ene (2n) According to general procedure, compound 2n was
prepared in 93% yield (0.93 mmol, 357mg) as white solid. 1H NMR
(400 MHz, CDCl3) δ 7.46 (s, 4H), 7.37 (d, J = 18.3 Hz, 2H), 6.18 (d, J =
18.4 Hz, 2H), 1.31 (s, 24H, CH3, 2Bpin). 13C NMR (100 MHz, CDCl3) δ
148.85, 137.94, 127.32, 83.39, 24.80. 11B NMR (128 MHz) δ 29.24.
(E)-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)aniline
(2o) According to general procedure, compound 2o was prepared in
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins