高等学校化学学报 ›› 2023, Vol. 44 ›› Issue (6): 20220714.doi: 10.7503/cjcu20220714
收稿日期:
2022-11-11
出版日期:
2023-06-10
发布日期:
2023-03-13
通讯作者:
南江
E-mail:nanjiang@sust.edu.cn
基金资助:
NAN Jiang(), LIU Shilei, HUANG Guanjie
Received:
2022-11-11
Online:
2023-06-10
Published:
2023-03-13
Contact:
NAN Jiang
E-mail:nanjiang@sust.edu.cn
Supported by:
摘要:
使用廉价易得的亚胺化合物在In(OTf)3与氧化剂串联条件下进行[3+2+1]环化反应, 实现了亚胺分子的新化学转化模式, 最终以良好至优秀的产率合成了23种结构新颖的吖啶衍生物. 该方法条件简单, 具有良好的底物适用性与基团兼容性, 为在光电材料领域广泛应用的吖啶化合物的合成提供了一种新途径.
中图分类号:
TrendMD:
南江, 刘石磊, 黄冠杰. In(OTf)3催化双亚胺分子间环化反应合成吖啶. 高等学校化学学报, 2023, 44(6): 20220714.
NAN Jiang, LIU Shilei, HUANG Guanjie. In(OTf)3-catalyzed Intermolecular [3+2+1] Cyclization of Two Imine Units. Chem. J. Chinese Universities, 2023, 44(6): 20220714.
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|---|
2a | White solid | 83 | 294—301 | 356.1439(356.1431) |
2b | White solid | 64 | 260—265 | 370.1596(370.1587) |
2c | White solid | 68 | 260—263 | 412.2065(412.2059) |
2d | White solid | 64 | 265—270 | 386.1545(386.1534) |
2e | White solid | 54 | 245—252 | 402.1316(402.1309) |
2f | White solid | 60 | 253—255 | 432.1752(432.1742) |
2g | White solid | 72 | 200—203 | 390.1050(390.1036) |
2h | White solid | 65 | 279—280 | 374.1345(374.1331) |
2i | White solid | 70 | 286—288 | 424.1313(424.1301) |
2j | White solid | 78 | 254—256 | 456.1034(456.1028) |
2k | White solid | 66 | 350—354 | 381.1392(381.1383) |
2l | Yellow solid | 70 | 301—306 | 401.1290(401.1283) |
2m | White solid | 66 | 266—270 | 434.0544(434.0535) |
2n | Yellow solid | 69 | 262—265 | 482.0406(482.0391) |
2o | Yellow solid | 64 | 250—254 | 434.0544(434.0536) |
2p | White solid | 65 | 290—393 | 452.0450(452.0441) |
2q | White solid | 69 | 270—272 | 384.1752(384.1743) |
2r | White solid | 62 | 240—243 | 416.1651(416.1644) |
2s | White solid | 53 | 313—315 | 406.1596(406.1587) |
2t | Yellow solid | 66 | 251—253 | 362.1003(362.0994) |
2u | White solid | 58 | 270—275 | 384.1752(384.1741) |
2v | Yellow solid | 40 | 334—336 | 508.2065(508.2057) |
2w | Yellow solid | 67 | 350—355 | 511.9649(511.9636) |
1a′ | White solid | 65 | 255—258 | 358.1596(358.1589) |
3a′ | Yellow solid | 17 | 276—280 | 358.1433(358.1455) |
5a | Yellow solid | 79 | 355—358 | 432.1747(432.1744) |
Table 1 Appearance, yields, melting points(m. p.) and HRMS data of compounds 2a—2w
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|---|
2a | White solid | 83 | 294—301 | 356.1439(356.1431) |
2b | White solid | 64 | 260—265 | 370.1596(370.1587) |
2c | White solid | 68 | 260—263 | 412.2065(412.2059) |
2d | White solid | 64 | 265—270 | 386.1545(386.1534) |
2e | White solid | 54 | 245—252 | 402.1316(402.1309) |
2f | White solid | 60 | 253—255 | 432.1752(432.1742) |
2g | White solid | 72 | 200—203 | 390.1050(390.1036) |
2h | White solid | 65 | 279—280 | 374.1345(374.1331) |
2i | White solid | 70 | 286—288 | 424.1313(424.1301) |
2j | White solid | 78 | 254—256 | 456.1034(456.1028) |
2k | White solid | 66 | 350—354 | 381.1392(381.1383) |
2l | Yellow solid | 70 | 301—306 | 401.1290(401.1283) |
2m | White solid | 66 | 266—270 | 434.0544(434.0535) |
2n | Yellow solid | 69 | 262—265 | 482.0406(482.0391) |
2o | Yellow solid | 64 | 250—254 | 434.0544(434.0536) |
2p | White solid | 65 | 290—393 | 452.0450(452.0441) |
2q | White solid | 69 | 270—272 | 384.1752(384.1743) |
2r | White solid | 62 | 240—243 | 416.1651(416.1644) |
2s | White solid | 53 | 313—315 | 406.1596(406.1587) |
2t | Yellow solid | 66 | 251—253 | 362.1003(362.0994) |
2u | White solid | 58 | 270—275 | 384.1752(384.1741) |
2v | Yellow solid | 40 | 334—336 | 508.2065(508.2057) |
2w | Yellow solid | 67 | 350—355 | 511.9649(511.9636) |
1a′ | White solid | 65 | 255—258 | 358.1596(358.1589) |
3a′ | Yellow solid | 17 | 276—280 | 358.1433(358.1455) |
5a | Yellow solid | 79 | 355—358 | 432.1747(432.1744) |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ |
---|---|---|
2a | 8.11(d, J=9.3 Hz, 2H), 8.02(d, J=8.8 Hz, 2H), 7.90(d, J=7.8 Hz, 2H), 7.78—7.68(m, 3H), 7.55—7.46(m, 4H), 7.24(d, J=8.7 Hz, 2H), 7.11(t, J=7.9 Hz, 2H) | 148.4, 143.3, 133.5, 132.5, 130.8, 130.6, 130.0, 128.9, 128.8, 128.7, 128.3, 126.4, 125.3, 122.5 |
2b | 8.16(d, J=9.1 Hz, 2H), 8.01(d, J=9.2 Hz, 2H), 7.87(d, J=7.8 Hz, 2H), 7.54—7.45(m, 4H), 7.36(d, J=8.6 Hz, 2H), 7.30(d, J=8.6 Hz, 2H), 7.11(t, J=8.7 Hz, 2H), 2.66(s, 3H) | 147.9, 147.4, 140.0, 138.9, 133.4, 133.0, 131.6, 130.6, 129.6, 128.9, 128.8, 127.1, 126.5, 125.4, 122.9, 21.6 |
2c | 8.10(d, J=8.9 Hz, 2H), 8.00(d, J=9.0 Hz, 2H), 7.88(d, J=7.8 Hz, 2H), 7.74(d, J=7.4 Hz, 2H), 7.48(t, J=7.4 Hz, 2H), 7.43(d, J=8.2 Hz, 2H), 7.29(d, J=8.9 Hz, 2H), 7.08(t, J=7.9 Hz, 2H), 1.59(s, 9H) | 152.6, 148.4, 146.7, 140.2, 133.4, 132.4, 130.8, 129.4, 129.0, 128.7, 128.3, 127.7, 126.3, 125.2, 122.7, 35.0, 31.6 |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ |
2d | 8.07(d, J=8.9 Hz, 2H), 7.99(d, J=9.2 Hz, 2H), 7.89(d, J=7.7 Hz, 2H), 7.54—7.45(m, 2H), 7.44—7.33(m, 4H), 7.29—7.21(m, 2H), 7.21—7.10(m, 2H), 4.06(s, 3H) | 160.3, 148.4, 146.3, 135.3, 133.5, 132.5, 131.0, 130.8, 128.9, 128.8, 128.2, 126.4, 125.4, 122.9, 116.4, 55.6 |
2e | 8.07(d, J=9.0 Hz, 2H), 8.01(d, J=9.0 Hz, 2H), 7.90(d, J=7.8 Hz, 2H), 7.59(d, J=7.9 Hz, 2H), 7.51(t, J=7.4 Hz, 2H), 7.43(d, J=7.9 Hz, 2H), 7.37(d, J=8.6 Hz, 2H), 7.17(t, J=8.6 Hz, 2H), 2.72(s, 3H) | 148.4, 145.7, 139.9, 139.8, 133.5, 132.4, 130.6, 130.5, 128.9, 128.7, 128.6, 128.3, 126.5, 125.3, 122.6, 15.9 |
2f | 8.10(d, J=9.0 Hz, 2H), 8.05—7.95(m, 4H), 7.90(d, J=7.7 Hz, 4H), 7.64—7.39(m, 9H), 7.11(t, J=8.0 Hz, 2H) | 148.5, 146.0, 142.2, 141.6, 140.4, 133.5, 132.5, 130.7, 130.5, 129.3, 129.0, 129.0, 128.8, 128.4, 127.8, 127.1, 126.5, 125.3, 122.5 |
2g | 8.13—7.88(m, 6H), 7.76—7.68(m, 2H), 7.58—7.46(m, 4H), 7.30—7.14(m, 4H) | 147.5, 145.9, 141.3, 135.2, 133.4, 133.3, 131.5, 131.1, 130.0, 128.9, 128.6, 126.8, 126.5, 125.5, 122.5 |
2h | 8.40—8.23(m, 2H), 8.13(d, J=8.6 Hz, 2H), 7.96(d, J=7.8 Hz, 2H), 7.62—7.45(m, 6H), 7.28—7.16(m, 4H) | 138.3, 135.2, 133.4, 131.4, 131.3, 129.9, 129.5, 128.5, 127.4, 126.3, 123.1, 122.9 |
2i | 8.08(d, J=9.0 Hz, 2H), 8.04—7.95(m, 4H), 7.91(d, J=7.8 Hz, 2H), 7.69(d, J=7.9 Hz, 2H), 7.54—7.47(m, 2H), 7.11(d, J=4.0 Hz, 4H) | 148.4, 147.2, 144.3, 133.6, 132.6, 131.3(q, J=32.4 Hz), 130.9, 130.1, 128.9, 128.7, 128.3, 127.6 |
2j | 8.08(d, J=9.1 Hz, 2H), 8.01(d, J=8.2 Hz, 4H), 7.90(d, J=7.8 Hz, 2H), 7.62(d, J=6.9 Hz, 2H), 7.51(t, J=7.4 Hz, 2H), 7.17(d, J=8.7 Hz, 2H), 7.14—7.06(m, 2H) | 128.9, 128.8, 128.3, 126.7, 125.3, 125.3, 122.0 |
2k | 8.16(d, J=9.0 Hz, 2H), 8.07—7.86(m, 6H), 7.67(d, J=9.0 Hz, 2H), 7.51(t, J=7.4 Hz, 2H), 7.18—7.00(m, 4H) | 148.0, 147.7, 144.6, 134.3, 133.5, 133.3, 131.3, 129.5, 129.1, 128.5, 127.0, 126.6, 125.5, 121.9, 118.3, 112.9 |
2l | 8.45(d, J=8.0 Hz, 2H), 7.96(d, J=9.6 Hz, 2H), 7.90(d, J=9.1 Hz, 2H), 7.80(d, J=7.8 Hz, 2H), 7.64(d, J=8.2 Hz, 2H), 7.40(t, J=7.4 Hz, 2H), 7.03—6.93(m, 4H) | 148.4, 133.7, 132.8, 131.7, 129.7, 129.1, 128.6, 128.2, 127.0, 125.9, 125.5, 121.6 |
2m | 8.09(d, J=8.1 Hz, 2H), 8.03(d, J=9.2 Hz, 2H), 7.96—7.87(m, 3H), 7.70(s, 1H), 7.64—7.45(m, 4H), 7.28—7.14(m, 4H) | 148.3, 145.2, 144.4, 133.5, 132.9, 132.8, 132.4, 132.0, 130.2, 129.0, 128.8, 128.1, 126.8, 125.5, 124.7, 122.2 |
2n | 8.19(d, J=8.4 Hz, 2H), 8.10(d, J=7.5 Hz, 1H), 8.03(d, J=8.5 Hz, 2H), 7.93—7.83(m, 3H), 7.55—7.39(m, 4H), 7.24—7.11(m, 4H) | 147.5, 145.5, 145.0, 138.5, 138.1, 133.5, 133.4, 132.3, 129.9, 129.2, 129.0, 128.8, 126.9, 126.4, 125.7, 122.4, 96.0 |
2o | 8.14(d, J=9.1 Hz, 2H), 8.03(d, J=9.1 Hz, 2H), 8.00—7.95(m, 1H), 7.92(d, J=7.8 Hz, 2H), 7.68—7.45(m, 5H), 7.33—7.14(m, 4H) | 148.7, 144.5, 144.0, 134.7, 133.4, 132.6, 131.8, 130.6, 130.5, 129.8, 129.0, 128.6, 127.6, 126.7, 125.9, 124.5, 122.2 |
2p | 8.24—7.84(m, 7H), 7.61—7.48(m, 2H), 7.35—7.21(m, 6H) | 133.5, 133.4, 129.8, 129.1, 128.5, 127.3, 127.0, 126.7, 125.7, 122.2, 118.5 |
2q | 8.09(d, J=9.0 Hz, 2H), 7.99(d, J=9.0 Hz, 2H), 7.87(d, J=7.8 Hz, 2H), 7.48(t, J=7.0 Hz, 3H), 7.38(d, J=8.7 Hz, 2H), 7.29—7.20(m, 2H), 7.12(t, J=7.5 Hz, 2H), 2.59(s, 3H), 2.39(s, 3H) | 148.5, 146.9, 140.5, 139.3, 137.2, 133.5, 132.4, 132.0, 130.9, 130.8, 129.1, 128.6, 128.4, 127.1, 126.3, 125.2, 122.7, 19.8, 19.8 |
2r | 8.04(d, J=9.0 Hz, 2H), 7.92(d, J=9.0 Hz, 2H), 7.81(d, J=7.7 Hz, 2H), 7.44(t, J=7.4 Hz, 2H), 7.38(d, J=8.7 Hz, 2H), 7.18—7.10(m, 3H), 7.02—6.94(m, 2H), 4.08(s, 3H), 3.73(s, 3H) | 151.5, 149.9, 148.4, 146.2, 135.4, 133.4, 132.5, 130.7, 128.9, 128.7, 128.3, 126.5, 125.4, 122.8, 122.2, 113.6, 113.1, 56.2, 56.2 |
2s | 8.23(d, J=8.4 Hz, 1H), 8.16—8.08(m, 3H), 8.02(d, J=8.2 Hz, 2H), 7.98(s, 1H), 7.88(d, J=7.9 Hz, 2H), 7.83(d, J=8.1 Hz, 1H), 7.74—7.65(m, 2H), 7.62(t, J=7.6 Hz, 1H), 7.42(t, J=7.5 Hz, 2H), 7.19(d, J=8.7 Hz, 2H), 6.89(t, J=8.2 Hz, 2H) | 147.1, 139.9, 134.7, 133.7, 133.3, 133.3, 130.7, 130.2, 128.8, 128.8, 128.7, 128.4, 128.1, 127.5, 126.9, 126.8, 126.7, 125.9, 125.5, 123.0 |
2t | 8.08(d, J=9.2 Hz, 2H), 8.02(d, J=9.3 Hz, 2H), 7.95—7.80(m, 3H), 7.60—7.42(m, 5H), 7.30—7.18(m, 3H) | 148.3, 144.4, 138.3, 133.5, 132.7, 130.3, 129.5, 128.9, 128.8, 128.3, 128.1, 128.1, 126.8, 125.6, 123.9 |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ |
2u | 8.06(d, J=9.1 Hz, 2H), 7.91(d, J=9.1 Hz, 2H), 7.76—7.63(m, 5H), 7.50(d, J=6.2 Hz, 2H), 7.11(d, J=8.8 Hz, 2H), 6.93(d, J=8.8 Hz, 2H), 2.48(s, 6H) | 148.1, 145.7, 143.6, 136.3, 133.7, 132.2, 130.8, 130.0, 128.7, 128.7, 128.6, 128.4, 128.4, 126.9, 122.6, 21.0 |
2v | 8.18—8.00(m, 6H), 7.82—7.69(m, 7H), 7.58(d, J=7.1 Hz, 2H), 7.51(t, J=7.5 Hz, 4H), 7.45—7.36(m, 4H), 7.31—7.28(m, 2H) | 148.5, 146.4, 143.2, 140.0, 138.9, 133.9, 132.9, 131.0, 129.9, 129.7, 129.4, 128.9, 128.7, 127.7, 127.2, 126.7, 124.4, 122.6 |
2w | 8.16—8.00(m, 4H), 7.96—7.68(m, 5H), 7.48(d, J=7.0 Hz, 2H), 7.20(d, J=9.3 Hz, 2H), 7.12—7.03(m, 2H) | 140.4, 139.9, 135.1, 127.7, 124.9, 123.9, 123.7, 123.0, 122.3, 122.1, 121.7, 121.3, 120.8, 115.4, 113.7 |
1a′ | 8.50(d, J=8.5 Hz, 2H), 7.85(d, J=8.1 Hz, 2H), 7.75(d, J=8.7 Hz, 2H), 7.65(t, J=7.8 Hz, 2H), 7.59(d, J=7.8 Hz, 2H), 7.42(t, J=7.6 Hz, 2H), 7.20(t, J=7.7 Hz, 2H), 7.12(d, J=8.7 Hz, 2H), 7.06(t, J=7.5 Hz, 1H), 6.80(s, 1H), 6.46(s, 1H) | 146.1, 136.0, 132.2, 130.3, 128.8, 128.4, 128.3, 127.9, 126.9, 126.2, 123.0, 122.2, 116.8, 114.6, 39.1 |
3a′ | 8.49(d, J=7.4 Hz, 2H), 7.98—7.78(m, 4H), 7.74—7.41(m, 8H), 7.24(t, J=7.4 Hz, 2H), 7.08(t, J=7.4 Hz, 1H), 6.58(s, 1H) | 148.8, 145.1, 131.5, 131.1, 128.9, 128.8, 128.5, 128.3, 126.8, 126.4, 124.3, 122.8, 118.1, 117.4, 38.1 |
5a | 8.26(d, J=9.3 Hz, 2H), 8.00(d, J=7.8 Hz, 2H), 7.94—7.82(m, 4H), 7.70(m, 4H), 7.68—7.57(m, 4H), 7.39—7.22(m, 6H) | 156.2, 142.7, 140.7, 140.4, 138.3, 132.4, 132.0, 131.7, 131.5, 130.7, 129.9, 129.4, 129.3, 129.1, 128.9, 128.3, 128.0, 125.0, 117.1 |
Table 2 1H NMR and 13C NMR data of compounds 2a—2w*
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ |
---|---|---|
2a | 8.11(d, J=9.3 Hz, 2H), 8.02(d, J=8.8 Hz, 2H), 7.90(d, J=7.8 Hz, 2H), 7.78—7.68(m, 3H), 7.55—7.46(m, 4H), 7.24(d, J=8.7 Hz, 2H), 7.11(t, J=7.9 Hz, 2H) | 148.4, 143.3, 133.5, 132.5, 130.8, 130.6, 130.0, 128.9, 128.8, 128.7, 128.3, 126.4, 125.3, 122.5 |
2b | 8.16(d, J=9.1 Hz, 2H), 8.01(d, J=9.2 Hz, 2H), 7.87(d, J=7.8 Hz, 2H), 7.54—7.45(m, 4H), 7.36(d, J=8.6 Hz, 2H), 7.30(d, J=8.6 Hz, 2H), 7.11(t, J=8.7 Hz, 2H), 2.66(s, 3H) | 147.9, 147.4, 140.0, 138.9, 133.4, 133.0, 131.6, 130.6, 129.6, 128.9, 128.8, 127.1, 126.5, 125.4, 122.9, 21.6 |
2c | 8.10(d, J=8.9 Hz, 2H), 8.00(d, J=9.0 Hz, 2H), 7.88(d, J=7.8 Hz, 2H), 7.74(d, J=7.4 Hz, 2H), 7.48(t, J=7.4 Hz, 2H), 7.43(d, J=8.2 Hz, 2H), 7.29(d, J=8.9 Hz, 2H), 7.08(t, J=7.9 Hz, 2H), 1.59(s, 9H) | 152.6, 148.4, 146.7, 140.2, 133.4, 132.4, 130.8, 129.4, 129.0, 128.7, 128.3, 127.7, 126.3, 125.2, 122.7, 35.0, 31.6 |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ |
2d | 8.07(d, J=8.9 Hz, 2H), 7.99(d, J=9.2 Hz, 2H), 7.89(d, J=7.7 Hz, 2H), 7.54—7.45(m, 2H), 7.44—7.33(m, 4H), 7.29—7.21(m, 2H), 7.21—7.10(m, 2H), 4.06(s, 3H) | 160.3, 148.4, 146.3, 135.3, 133.5, 132.5, 131.0, 130.8, 128.9, 128.8, 128.2, 126.4, 125.4, 122.9, 116.4, 55.6 |
2e | 8.07(d, J=9.0 Hz, 2H), 8.01(d, J=9.0 Hz, 2H), 7.90(d, J=7.8 Hz, 2H), 7.59(d, J=7.9 Hz, 2H), 7.51(t, J=7.4 Hz, 2H), 7.43(d, J=7.9 Hz, 2H), 7.37(d, J=8.6 Hz, 2H), 7.17(t, J=8.6 Hz, 2H), 2.72(s, 3H) | 148.4, 145.7, 139.9, 139.8, 133.5, 132.4, 130.6, 130.5, 128.9, 128.7, 128.6, 128.3, 126.5, 125.3, 122.6, 15.9 |
2f | 8.10(d, J=9.0 Hz, 2H), 8.05—7.95(m, 4H), 7.90(d, J=7.7 Hz, 4H), 7.64—7.39(m, 9H), 7.11(t, J=8.0 Hz, 2H) | 148.5, 146.0, 142.2, 141.6, 140.4, 133.5, 132.5, 130.7, 130.5, 129.3, 129.0, 129.0, 128.8, 128.4, 127.8, 127.1, 126.5, 125.3, 122.5 |
2g | 8.13—7.88(m, 6H), 7.76—7.68(m, 2H), 7.58—7.46(m, 4H), 7.30—7.14(m, 4H) | 147.5, 145.9, 141.3, 135.2, 133.4, 133.3, 131.5, 131.1, 130.0, 128.9, 128.6, 126.8, 126.5, 125.5, 122.5 |
2h | 8.40—8.23(m, 2H), 8.13(d, J=8.6 Hz, 2H), 7.96(d, J=7.8 Hz, 2H), 7.62—7.45(m, 6H), 7.28—7.16(m, 4H) | 138.3, 135.2, 133.4, 131.4, 131.3, 129.9, 129.5, 128.5, 127.4, 126.3, 123.1, 122.9 |
2i | 8.08(d, J=9.0 Hz, 2H), 8.04—7.95(m, 4H), 7.91(d, J=7.8 Hz, 2H), 7.69(d, J=7.9 Hz, 2H), 7.54—7.47(m, 2H), 7.11(d, J=4.0 Hz, 4H) | 148.4, 147.2, 144.3, 133.6, 132.6, 131.3(q, J=32.4 Hz), 130.9, 130.1, 128.9, 128.7, 128.3, 127.6 |
2j | 8.08(d, J=9.1 Hz, 2H), 8.01(d, J=8.2 Hz, 4H), 7.90(d, J=7.8 Hz, 2H), 7.62(d, J=6.9 Hz, 2H), 7.51(t, J=7.4 Hz, 2H), 7.17(d, J=8.7 Hz, 2H), 7.14—7.06(m, 2H) | 128.9, 128.8, 128.3, 126.7, 125.3, 125.3, 122.0 |
2k | 8.16(d, J=9.0 Hz, 2H), 8.07—7.86(m, 6H), 7.67(d, J=9.0 Hz, 2H), 7.51(t, J=7.4 Hz, 2H), 7.18—7.00(m, 4H) | 148.0, 147.7, 144.6, 134.3, 133.5, 133.3, 131.3, 129.5, 129.1, 128.5, 127.0, 126.6, 125.5, 121.9, 118.3, 112.9 |
2l | 8.45(d, J=8.0 Hz, 2H), 7.96(d, J=9.6 Hz, 2H), 7.90(d, J=9.1 Hz, 2H), 7.80(d, J=7.8 Hz, 2H), 7.64(d, J=8.2 Hz, 2H), 7.40(t, J=7.4 Hz, 2H), 7.03—6.93(m, 4H) | 148.4, 133.7, 132.8, 131.7, 129.7, 129.1, 128.6, 128.2, 127.0, 125.9, 125.5, 121.6 |
2m | 8.09(d, J=8.1 Hz, 2H), 8.03(d, J=9.2 Hz, 2H), 7.96—7.87(m, 3H), 7.70(s, 1H), 7.64—7.45(m, 4H), 7.28—7.14(m, 4H) | 148.3, 145.2, 144.4, 133.5, 132.9, 132.8, 132.4, 132.0, 130.2, 129.0, 128.8, 128.1, 126.8, 125.5, 124.7, 122.2 |
2n | 8.19(d, J=8.4 Hz, 2H), 8.10(d, J=7.5 Hz, 1H), 8.03(d, J=8.5 Hz, 2H), 7.93—7.83(m, 3H), 7.55—7.39(m, 4H), 7.24—7.11(m, 4H) | 147.5, 145.5, 145.0, 138.5, 138.1, 133.5, 133.4, 132.3, 129.9, 129.2, 129.0, 128.8, 126.9, 126.4, 125.7, 122.4, 96.0 |
2o | 8.14(d, J=9.1 Hz, 2H), 8.03(d, J=9.1 Hz, 2H), 8.00—7.95(m, 1H), 7.92(d, J=7.8 Hz, 2H), 7.68—7.45(m, 5H), 7.33—7.14(m, 4H) | 148.7, 144.5, 144.0, 134.7, 133.4, 132.6, 131.8, 130.6, 130.5, 129.8, 129.0, 128.6, 127.6, 126.7, 125.9, 124.5, 122.2 |
2p | 8.24—7.84(m, 7H), 7.61—7.48(m, 2H), 7.35—7.21(m, 6H) | 133.5, 133.4, 129.8, 129.1, 128.5, 127.3, 127.0, 126.7, 125.7, 122.2, 118.5 |
2q | 8.09(d, J=9.0 Hz, 2H), 7.99(d, J=9.0 Hz, 2H), 7.87(d, J=7.8 Hz, 2H), 7.48(t, J=7.0 Hz, 3H), 7.38(d, J=8.7 Hz, 2H), 7.29—7.20(m, 2H), 7.12(t, J=7.5 Hz, 2H), 2.59(s, 3H), 2.39(s, 3H) | 148.5, 146.9, 140.5, 139.3, 137.2, 133.5, 132.4, 132.0, 130.9, 130.8, 129.1, 128.6, 128.4, 127.1, 126.3, 125.2, 122.7, 19.8, 19.8 |
2r | 8.04(d, J=9.0 Hz, 2H), 7.92(d, J=9.0 Hz, 2H), 7.81(d, J=7.7 Hz, 2H), 7.44(t, J=7.4 Hz, 2H), 7.38(d, J=8.7 Hz, 2H), 7.18—7.10(m, 3H), 7.02—6.94(m, 2H), 4.08(s, 3H), 3.73(s, 3H) | 151.5, 149.9, 148.4, 146.2, 135.4, 133.4, 132.5, 130.7, 128.9, 128.7, 128.3, 126.5, 125.4, 122.8, 122.2, 113.6, 113.1, 56.2, 56.2 |
2s | 8.23(d, J=8.4 Hz, 1H), 8.16—8.08(m, 3H), 8.02(d, J=8.2 Hz, 2H), 7.98(s, 1H), 7.88(d, J=7.9 Hz, 2H), 7.83(d, J=8.1 Hz, 1H), 7.74—7.65(m, 2H), 7.62(t, J=7.6 Hz, 1H), 7.42(t, J=7.5 Hz, 2H), 7.19(d, J=8.7 Hz, 2H), 6.89(t, J=8.2 Hz, 2H) | 147.1, 139.9, 134.7, 133.7, 133.3, 133.3, 130.7, 130.2, 128.8, 128.8, 128.7, 128.4, 128.1, 127.5, 126.9, 126.8, 126.7, 125.9, 125.5, 123.0 |
2t | 8.08(d, J=9.2 Hz, 2H), 8.02(d, J=9.3 Hz, 2H), 7.95—7.80(m, 3H), 7.60—7.42(m, 5H), 7.30—7.18(m, 3H) | 148.3, 144.4, 138.3, 133.5, 132.7, 130.3, 129.5, 128.9, 128.8, 128.3, 128.1, 128.1, 126.8, 125.6, 123.9 |
Compd. | 1H NMR(400 MHz), δ | 13C NMR(100 MHz), δ |
2u | 8.06(d, J=9.1 Hz, 2H), 7.91(d, J=9.1 Hz, 2H), 7.76—7.63(m, 5H), 7.50(d, J=6.2 Hz, 2H), 7.11(d, J=8.8 Hz, 2H), 6.93(d, J=8.8 Hz, 2H), 2.48(s, 6H) | 148.1, 145.7, 143.6, 136.3, 133.7, 132.2, 130.8, 130.0, 128.7, 128.7, 128.6, 128.4, 128.4, 126.9, 122.6, 21.0 |
2v | 8.18—8.00(m, 6H), 7.82—7.69(m, 7H), 7.58(d, J=7.1 Hz, 2H), 7.51(t, J=7.5 Hz, 4H), 7.45—7.36(m, 4H), 7.31—7.28(m, 2H) | 148.5, 146.4, 143.2, 140.0, 138.9, 133.9, 132.9, 131.0, 129.9, 129.7, 129.4, 128.9, 128.7, 127.7, 127.2, 126.7, 124.4, 122.6 |
2w | 8.16—8.00(m, 4H), 7.96—7.68(m, 5H), 7.48(d, J=7.0 Hz, 2H), 7.20(d, J=9.3 Hz, 2H), 7.12—7.03(m, 2H) | 140.4, 139.9, 135.1, 127.7, 124.9, 123.9, 123.7, 123.0, 122.3, 122.1, 121.7, 121.3, 120.8, 115.4, 113.7 |
1a′ | 8.50(d, J=8.5 Hz, 2H), 7.85(d, J=8.1 Hz, 2H), 7.75(d, J=8.7 Hz, 2H), 7.65(t, J=7.8 Hz, 2H), 7.59(d, J=7.8 Hz, 2H), 7.42(t, J=7.6 Hz, 2H), 7.20(t, J=7.7 Hz, 2H), 7.12(d, J=8.7 Hz, 2H), 7.06(t, J=7.5 Hz, 1H), 6.80(s, 1H), 6.46(s, 1H) | 146.1, 136.0, 132.2, 130.3, 128.8, 128.4, 128.3, 127.9, 126.9, 126.2, 123.0, 122.2, 116.8, 114.6, 39.1 |
3a′ | 8.49(d, J=7.4 Hz, 2H), 7.98—7.78(m, 4H), 7.74—7.41(m, 8H), 7.24(t, J=7.4 Hz, 2H), 7.08(t, J=7.4 Hz, 1H), 6.58(s, 1H) | 148.8, 145.1, 131.5, 131.1, 128.9, 128.8, 128.5, 128.3, 126.8, 126.4, 124.3, 122.8, 118.1, 117.4, 38.1 |
5a | 8.26(d, J=9.3 Hz, 2H), 8.00(d, J=7.8 Hz, 2H), 7.94—7.82(m, 4H), 7.70(m, 4H), 7.68—7.57(m, 4H), 7.39—7.22(m, 6H) | 156.2, 142.7, 140.7, 140.4, 138.3, 132.4, 132.0, 131.7, 131.5, 130.7, 129.9, 129.4, 129.3, 129.1, 128.9, 128.3, 128.0, 125.0, 117.1 |
Entry | Catalyst | Solvent | Temperture/℃ | Yield(%) |
---|---|---|---|---|
1 | DCE | 120 | 0 | |
2 | In(OTf)3 | DCE | 120 | 22 |
3 | Cu(OTf)2 | DCE | 120 | 18 |
4 | Sc(OTf)3 | DCE | 120 | 32 |
5 | Fe(acac)3 | DCE | 120 | Trace |
6 | Zn(OAc)2 | DCE | 120 | Trace |
7 | Ni(PPh3)2Cl | DCE | 120 | Trace |
8 | In(OTf)3 | EG | 120 | 83 |
9 | In(OTf)3 | EtOH | 120 | 52 |
10 | In(OTf)3 | HFIP | 120 | 30 |
11 | In(OTf)3 | DMSO | 120 | Trace |
12 | In(OTf)3 | DMF | 120 | Trace |
13 | In(OTf)3 | THF | 120 | 25 |
14 | In(OTf)3 | MeOH | 120 | 20 |
15 | In(OTf)3 | EG | 80 | 52 |
16 | In(OTf)3 | EG | 100 | 70 |
17 | In(OTf)3 | EG | 140 | 68 |
Table 3 Optimization of reaction conditions*
Entry | Catalyst | Solvent | Temperture/℃ | Yield(%) |
---|---|---|---|---|
1 | DCE | 120 | 0 | |
2 | In(OTf)3 | DCE | 120 | 22 |
3 | Cu(OTf)2 | DCE | 120 | 18 |
4 | Sc(OTf)3 | DCE | 120 | 32 |
5 | Fe(acac)3 | DCE | 120 | Trace |
6 | Zn(OAc)2 | DCE | 120 | Trace |
7 | Ni(PPh3)2Cl | DCE | 120 | Trace |
8 | In(OTf)3 | EG | 120 | 83 |
9 | In(OTf)3 | EtOH | 120 | 52 |
10 | In(OTf)3 | HFIP | 120 | 30 |
11 | In(OTf)3 | DMSO | 120 | Trace |
12 | In(OTf)3 | DMF | 120 | Trace |
13 | In(OTf)3 | THF | 120 | 25 |
14 | In(OTf)3 | MeOH | 120 | 20 |
15 | In(OTf)3 | EG | 80 | 52 |
16 | In(OTf)3 | EG | 100 | 70 |
17 | In(OTf)3 | EG | 140 | 68 |
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