Vol. 29, No. 9, 2018
Silva et al.
1781
4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane (3a)
Yield: 50 mg (97%); oil; 1H NMR (400 MHz, CDCl3)
d 7.83 (d, J 7.2 Hz, 2H, Haryl), 7.47 (t, J 7.2 Hz, 1H, Haryl),
7.38 (dd, J 7.2 and 6.8 Hz, 2H, Haryl), 1.36 (s, 12H, CH3);
13C NMR (100 MHz, CDCl3) d 134.7, 131.2, 127.7, 83.8,
2-(3-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-
borolane (3f)
Yield: 38 mg (65%); oil; 1H NMR (400 MHz, CDCl3)
d 7.72 (dd, J 7.2 and 1.6 Hz, 1H, Haryl), 7.43-7.39 (m,
1H, Haryl), 6.96 (dd, J 7.6 and 6.8 Hz, 1H, Haryl), 6.87 (d,
J 8.4 Hz, 1H, Haryl), 3.84 (s, 3H, OCH3), 1.38 (s, 12H, CH3);
13C NMR (100 MHz, CDCl3) d 164.0, 136.6, 132.3, 120.0,
110.3, 83.3, 55.6, 24.7; 11B NMR (128 MHz, CDCl3) d 28.4
(s). This is in agreement with data previously reported.24
11
24.9; B NMR (128 MHz, CDCl3) d 30.9 (s). This is in
agreement with data previously reported.18
4,4,5,5-Tetramethyl-2-(naphthalen-2-yl)-1,3,2-dioxa-
borolane (3b)
Yield: 57 mg (90%); waxy solid; 1H NMR (400 MHz,
CDCl3) d 8.79 (dd, J 8.8 and 0.8 Hz, 1H, Haryl), 8.11 (dd,
J 7.2 and 1.6 Hz, 1H, Haryl), 7.95 (d, J 8.4 Hz, 1H, Haryl),
7.86 (dd, J 8.0 and 0.8 Hz, 1H, Haryl), 7.58-7.54 (m, 1H,
Haryl), 7.51-7.47 (m, 2H, Haryl), 1.45 (s, 12H, CH3); 13C NMR
(100 MHz, CDCl3) d 136.9, 135.6, 133.2, 131.6, 128.4,
128.3, 126.3, 125.4, 124.9, 83.7, 24.9; 11B NMR (128 MHz,
CDCl3) d 31.4 (s). This is in agreement with data previously
reported.22
2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-
borolane (3g)
Yield: 41 mg (70%); oil; 1H NMR (400 MHz, CDCl3)
d 7.78 (d, J 8.8 Hz, 2H, Haryl), 6.91 (d, J 8.4 Hz, 2H,
13
Haryl), 3.83 (s, 3H, OCH3), 1.35 (s, 12H, CH3); C NMR
(100 MHz, CDCl3) d 162.1, 136.4, 113.2, 83.4, 54.9, 24.8;
11B NMR (128 MHz, CDCl3) d 28.1 (s). This is in agreement
with data previously reported.24
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (3h)
o
2-(2,6-Dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-
borolane (3c)
Yield: 36 mg (65%); white solid; mp 114-116 C;
1H NMR (400 MHz, CDCl3) d 7.71 (d, J 8.4 Hz, 2H, Haryl),
6.83 (d, J 8.4 Hz, 2H, Haryl), 6.32 (s, 1H, OH), 1.35 (s, 12H,
CH3); 13C NMR (100 MHz, CDCl3) d 158.6, 136.7, 114.9,
83.8, 24.7; 11B NMR (128 MHz, CDCl3) d 28.2 (s). This is
in agreement with data previously reported.25
Yield: 53.5 mg (92%); oil; 1H NMR (400 MHz, CDCl3)
d 6.98 (t, J 7.6 Hz, 1H, Haryl), 6.81 (d, J 7.6 Hz, 2H, Haryl),
2.28 (s, 6H, CH3), 1.22 (s, 12H, CH3); 13C NMR (100 MHz,
CDCl3) d 141.5, 128.9, 126.2, 83.3, 24.7, 22.0; 11B NMR
(128 MHz, CDCl3) d 32.3 (s). This is in agreement with
data previously reported.23
2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)
benzaldehyde (3i)
2-(4-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
(3d)
Yield: 53.5 mg (92%); oil; 1H NMR (400 MHz, CDCl3)
d 10.55 (s, 1H, CHO), 7.96 (dd, J 7.2 and 1.2 Hz, 1H,
Haryl), 7.86 (dd, J 7.2 and 1.6 Hz, 1H, Haryl), 7.61-7.54
Yield: 39 mg (70%); white solid; mp 51-52 oC; 1H NMR
(400 MHz, CDCl3) d 7.82 (t, J 7.2 Hz, 2H, Haryl), 7.06 (dd,
J 8.8 and 8.0 Hz, 2H, Haryl), 1.35 (s, 12H, CH3); 13C NMR
(100 MHz, CDCl3) d 165.1 (d, JC–F 248.9 Hz, Caryl), 136.9
(d, JC–F 8.4 Hz, Caryl), 114.7 (d, JC–F 20.5 Hz, Caryl), 83.8,
13
(m, 2H, Haryl), 1.40 (s, 12H, CH3); C NMR (100 MHz,
CDCl3) d 194.6, 141.2, 135.4, 132.9, 130.7, 127.8, 84.3,
11
24.8; B NMR (128 MHz, CDCl3) d 31.2 (s). This is in
agreement with data previously reported.26
11
19
24.8; B NMR (128 MHz, CDCl3) d 30.6 (s); F NMR
(376 MHz, CDCl3) d –108.4 (s). This is in agreement with
data previously reported.18
2-(Dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxa-
borolane (3j)
o
Yield: 44 mg (60%); white solid; mp 75-76 C;
2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxa-
borolane (3e)
1H NMR (400 MHz, CDCl3) d 7.96 (dd, J 8.0 and 1.6 Hz,
1H, Haryl), 7.85-7.80 (m, 2H, Haryl), 7.58 (d, J 8.4 Hz, 1H,
Haryl), 7.36-7.32 (m, 1H, Haryl), 7.26 (dd, J 7.6 and 7.2 Hz,
1H, Haryl), 7.21 (d, J 7.2 Hz, 1H, Haryl), 1.35 (s, 12H, CH3);
13C NMR (100 MHz, CDCl3) d 160.4, 156.3, 134.4, 126.9,
123.9, 123.6, 123.2, 122.4, 122.2, 120.3, 112.2, 84.0, 24.8;
11B NMR (128 MHz, CDCl3) d 30.6 (s). This is in agreement
with data previously reported.27
Yield: 44 mg (75%); oil; 1H NMR (400 MHz, CDCl3)
d 7.41 (d, J 7.6 Hz, 1H, Haryl), 7.34 (d, J 2.8 Hz, 1H,
Haryl), 7.32-7.26 (m, 1H, Haryl), 7.02 (ddd, J 8.0, 2.8 and
0.8 Hz, 1H, Haryl), 3.84 (s, 3H, OCH3), 1.35 (s, 12H, CH3);
13C NMR (100 MHz, CDCl3) d 158.9, 128.8, 127.1, 118.7,
117.7, 83.7, 55.1, 24.8; 11B NMR (128 MHz, CDCl3)
d 28.2 (s). This is in agreement with data previously
reported.24
4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane (3k)
Yield: 47.5 mg (82%); oil; 1H NMR (400 MHz, CDCl3)