Page 19 of 24
The Journal of Organic Chemistry
1
2
3
4
5
6
7
8
1
4,4,5,5-Tetramethyl-2-(1-phenyl-2-(p-tolyl)ethyl)-1,3,2-dioxaborolane (7oa). A colorless oil (46.7 mg, 72%). H NMR (400
MHz, CDCl3) δ 7.26 – 7.21 (m, 4H), 7.16 – 7.09 (m, 1H), 7.04 (dd, J = 19.6, 8.0 Hz, 4H), 3.12 (dd, J = 13.5, 9.6 Hz, 1H), 2.91 (dd,
J = 13.5, 7.0 Hz, 1H), 2.65 (dd, J = 9.6, 7.0 Hz, 1H), 2.28 (s, 3H), 1.11 (d, J = 2.5 Hz, 12H); 13C{1H} NMR (101 MHz, CDCl3) δ
142.6, 138.6, 135.0, 128.7, 128.3, 125.3, 83.3, 38.3, 24.5, 21.0; ATRꢀFTIR (cmꢀ1): 2978, 2925, 1595, 1451, 1360, 1326, 1240, 1142,
1088, 967, 855, 700; HRMS m/z (ESI) calcd for C21H28BO2 (M + H)+ 322.2177, found 322.2179.
9
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
1
Methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (7pa)41. A colorless oil (18.2 mg, 31%). H NMR
(400 MHz, CDCl3) δ 7.30 – 7.19 (m, 5H), 7.19 – 7.12 (m, 1H), 3.65 (s, 3H), 2.90 (dd, J = 15.9, 9.8 Hz, 1H), 2.70 – 2.63 (m, 2H),
1.22 (s, 6H), 1.17 (s, 6H); 13C{1H} NMR (101 MHz, CDCl3) δ 173.8, 141.3, 128.5, 128.2, 125.7, 83.6, 51.6, 37.1, 24.5; ATRꢀFTIR
(cmꢀ1): 3061, 2977, 1736, 1637, 1371, 1324, 1261, 1171, 1140, 1050, 973, 846,766,701; HRMS m/z (ESI) calcd for C16H23BO4Na
(M + Na)+ 313.1582, found 313.1589.
4,4,5,5-Tetramethyl-2-(2-phenylpropan-2-yl)-1,3,2-dioxaborolane (7qa)37. A colorless oil (36.6 mg, 74%). 1H NMR (400 MHz,
CDCl3) δ 7.37 – 7.26 (m, 4H), 7.13 (ddd, J = 6.6, 3.2, 1.6 Hz, 1H), 1.35 (s, 6H), 1.20 (s, 12H); 13C{1H} NMR (101 MHz, CDCl3) δ
148.6, 128.1, 126.3, 125.0, 83.3, 25.6, 24.5; ATRꢀFTIR (cmꢀ1): 2872, 2802, 1432, 1344, 1208, 1192, 1054, 972, 838; HRMS m/z
(ESI) calcd for C15H24BO2 (M + H)+ 247.1864, found 247.1864.
1
4,4,5,5-Tetramethyl-2-(1-phenylcyclopentyl)-1,3,2-dioxaborolane (7ra). A white solid (33.9 mg, 63%). H NMR (400 MHz,
CDCl3): δ 7.31 – 7.22 (m, 5H), 7.14 – 7.07 (m, 1H), 2.32 (d, J = 8.2 Hz, 2H), 1.78 – 1.59 (m, 6H), 1.13 (s, 12H); 13C{1H} NMR
(101 MHz, CDCl3): δ 147.1, 127.9, 127.0, 124.7, 83.3, 35.2, 24.4; ATRꢀFTIR (cmꢀ1): 2973, 2864, 1446, 1374, 1354, 1312, 1111,
748, 700; HRMS m/z (ESI) calcd for C17H26BO2 (M + H)+ 273.2020, found 273.2026.
4,4,5,5-tetramethyl-2-(1-phenylcyclopentyl)-1,3,2-dioxaborolane (7sa)42. A colorless oil (31.4 mg, 60%). H NMR (400 MHz,
1
CDCl3) δ 7.34 – 7.27 (m, 3H), 7.21 – 7.10 (m, 2H), 1.87 (dq, J = 14.7, 7.4 Hz, 1H), 1.70 (dq, J = 14.6, 7.4 Hz, 1H), 1.20 (d, J = 3.3
Hz, 12H), 1.09 (s, 3H), 0.82 (t, J = 7.4 Hz, 3H); 13C{1H} NMR (101 MHz, CDCl3): δ 147.2, 127.7, 126.9, 126.8, 125.0, 83.3, 31.9,
24.6, 21.0, 1.0; ATRꢀFTIR (cmꢀ1): 2965, 2925, 1637, 1461, 1372, 1349, 1313, 1261, 1142, 1097, 1026, 801, 700; HRMS m/z (ESI)
calcd for C12H26BO2 (M + H)+ 261.2020, found 261.2022.
4,4,5,5-Tetramethyl-2-(1-phenylcyclopropyl)-1,3,2-dioxaborolane (7ta)43. A colorless oil (24.2 mg, 50%). H NMR (400 MHz,
1
CDCl3) δ 7.30 – 7.19 (m, 5H), 7.16 – 7.09 (m, 1H), 1.21 (s, 12H), 1.10 (q, J = 3.5 Hz, 2H), 0.90 (q, J = 3.5 Hz, 2H); 13C{1H} NMR
(101 MHz, CDCl3) δ 144.8, 128.9, 128.0, 125.2, 83.3, 24.6, 13.3; ATRꢀFTIR (cmꢀ1): 2946, 2932, 1643, 1421, 1353, 1312, 1127,
838, 737, 655; HRMS m/z (ESI) calcd for C15H22BO2 (M + H)+ 244.1635, found 244.1640.
N-(2,5-Dimethoxybenzyl)-N-(2-phenoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (10)44. A white solid
(90.2 mg, 84%). 1H NMR (400 MHz, CDCl3) δ 7.57 (dd, J = 7.0, 1.5 Hz, 2H), 7.31 (dd, J = 11.2, 4.7 Hz, 2H), 7.14 (t, J = 7.4 Hz,
1H), 6.99 (d, J = 3.0 Hz, 1H), 6.86 – 6.80 (m, 2H), 6.74 (d, J = 8.7 Hz, 1H), 6.68 (dt, J = 5.1, 2.5 Hz, 1H), 6.62 (d, J = 8.9 Hz, 1H),
4.98 (d, J = 12.0 Hz, 1H), 4.90 (d, J = 12.0 Hz, 1H), 3.63 (s, 3H), 3.50 (s, 3H), 1.97 (s, 3H), 1.32 (d, J = 4.7 Hz, 12H); 13C{1H}
ACS Paragon Plus Environment