Chem. J. Chinese Universities ›› 2016, Vol. 37 ›› Issue (2): 269.doi: 10.7503/cjcu20150465
• Organic Chemistry • Previous Articles Next Articles
Received:
2015-06-12
Online:
2016-02-10
Published:
2016-01-14
Contact:
TONG Mengliang
E-mail:13973327103@163.com
Supported by:
CLC Number:
TrendMD:
YAN Dong, TONG Mengliang. Metal-free Thiolation of C(sp3)—S Bond Adjacent to an Oxygen Atom†[J]. Chem. J. Chinese Universities, 2016, 37(2): 269.
Scheme 1 Thioetherification of Isochromans 3a: R=Me, Ar=Ph; 3b: R=Et, Ar=Ph; 3c: R=i-Pr, Ar=Ph; 3d: R=Ph, Ar=Ph; 3e: R=PhCO, Ar=Ph; 3f: R= Me, Ar=4-Me-Ph; 3g: R=Me, Ar=4-OMe-Ph; 3h: R=Me, Ar=4-Cl-Ph; 3i: R= Me, Ar=4-Me-Ph; 3j: R=i-Pr, Ar=Ph; 3k: R=i-Pr, Ar=4-Cl-Ph; 3l: R=—CH2CH2—, Ar=Ph; 3m: R=—CH2CH2—, Ar=4-Cl-Ph
Compd. | Appearance | m.p./℃ | HR-MS, m/z([M]+) | IR(KBr), |
---|---|---|---|---|
3a | Yellow oil | — | 230.0758 | 2956, 2854, 1645, 1479, 1387, 1022, 745, 698 |
3b | Yellow solid | 67—68 | 244.0913 | 2916, 2848, 1490, 1390, 1014, 810, 723 |
3c | Brown solid | 70—72 | 258.1071 | 2935, 2860, 1661, 1507, 1379, 1009, 793 |
3d | Pale yellow oil | — | 292.0918 | 3011, 1597, 1495, 1212, 1019, 798, 694 |
3e | Brown solid | 87—89 | 320.0866 | 2930, 1634, 1594, 1392, 1226, 1033, 783 |
3f | Yellow oil | — | 244.0913 | 3013, 2918, 2843, 1595, 1492, 1238, 1016, 785 |
3g | Brown solid | 72—74 | 260.0867 | 2923, 2841, 1593, 1498, 1236, 1012, 831 |
3h | Yellow solid | 77—78 | 264.0370 | 2917, 2851, 1478, 1389, 1261, 1101, 1008, 812 |
3i | Yellow oil | — | 272.1223 | 2941, 2876, 1497, 1354, 1242, 1104, 1011, 806 |
3j | Pale yellow oil | — | 288.1177 | 2923, 2824, 1596, 1369, 1198, 1016, 822, 697 |
3k | Yellow oil | — | 292.0678 | 2921, 2837, 1588, 1469, 1382, 1258, 1127, 996, 793 |
3l | Yellow solid | 84—86 | 242.0759 | 3012, 2923, 2844, 1596, 1389, 1244, 1012, 803, 698 |
3m | Yellow solid | 81—82 | 276.0368 | 3009, 2915, 2832, 1594, 1471, 1254, 1123, 1014, 798 |
Table 1 Appearance, melting points, HR-MS and IR data of compounds 3a—3m
Compd. | Appearance | m.p./℃ | HR-MS, m/z([M]+) | IR(KBr), |
---|---|---|---|---|
3a | Yellow oil | — | 230.0758 | 2956, 2854, 1645, 1479, 1387, 1022, 745, 698 |
3b | Yellow solid | 67—68 | 244.0913 | 2916, 2848, 1490, 1390, 1014, 810, 723 |
3c | Brown solid | 70—72 | 258.1071 | 2935, 2860, 1661, 1507, 1379, 1009, 793 |
3d | Pale yellow oil | — | 292.0918 | 3011, 1597, 1495, 1212, 1019, 798, 694 |
3e | Brown solid | 87—89 | 320.0866 | 2930, 1634, 1594, 1392, 1226, 1033, 783 |
3f | Yellow oil | — | 244.0913 | 3013, 2918, 2843, 1595, 1492, 1238, 1016, 785 |
3g | Brown solid | 72—74 | 260.0867 | 2923, 2841, 1593, 1498, 1236, 1012, 831 |
3h | Yellow solid | 77—78 | 264.0370 | 2917, 2851, 1478, 1389, 1261, 1101, 1008, 812 |
3i | Yellow oil | — | 272.1223 | 2941, 2876, 1497, 1354, 1242, 1104, 1011, 806 |
3j | Pale yellow oil | — | 288.1177 | 2923, 2824, 1596, 1369, 1198, 1016, 822, 697 |
3k | Yellow oil | — | 292.0678 | 2921, 2837, 1588, 1469, 1382, 1258, 1127, 996, 793 |
3l | Yellow solid | 84—86 | 242.0759 | 3012, 2923, 2844, 1596, 1389, 1244, 1012, 803, 698 |
3m | Yellow solid | 81—82 | 276.0368 | 3009, 2915, 2832, 1594, 1471, 1254, 1123, 1014, 798 |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
3a | 7.17—7.26(m, 10H), 5.67(s, 1H), 3.47(s, 3H) | 139.5, 138.0, 134.3, 133.2, 129.5, 128.1, 127.9, 126.4, 90.2, 56.8 |
3b | 7.31(dd, J=4.0, 2.9 Hz, 5H), 7.23(d, J=8.2 Hz, 2H), 7.06(m, 3H), 5.68(s, 1H), 3.42(m, 2H), 1.20(t, J=7.5 Hz, 3H) | 139.4, 138.1, 135.1, 133.2, 129.5, 128.1, 128.1, 127.2, 91.3, 58.2, 21.3 |
3c | 7.32—7.30(m, 5H), 7.23(d, J=8.2 Hz, 2H), 7.03(t, J=8.2 Hz, 3H), 5.97(s, 1H), 3.53(m, 1H), 1.29(s, 3H), 1.27(s, 3H) | 138.6, 133.7, 131.4, 129.7, 129.3, 129.0, 128.2, 126.3, 85.0, 73.5, 23.9, 23.8 |
3d | 7.34—7.28(m, 5H), 7.24—7.20(m, 5H), 7.11—7.08(t, J=8.2 Hz, 2H), 6.93—6.85(m, 3H), 6.07(s, 1H) | 146.5, 139.0, 134.5, 132.5, 132.3, 130.8, 130.7, 129.4, 129.3, 128.5, 127.6, 125.4, 119.8, 89.2 |
3e | 7.97(d, J=6.1 Hz, 2H), 7.47(t, J=7.4 Hz, 1H), 7.40(t, J=7.4 Hz, 2H), 7.35—7.15(m, 10H), 7.09(t, J=7.4 Hz, 1H) | 164.2, 138.9, 133.8, 133.3, 131.4, 131.3, 130.5, 129.8, 129.7, 129.7, 129.6, 129.4, 129.3, 128.8, 128.7, 128.6, 128.4, 125.9, 125.8, 85.3 |
3f | 7.48(d, J=7.8 Hz, 2H), 7.40—7.30(m, 1H), 7.26—7.00(m, 5H), 6.45(s, 1H), 4.55—4.52(m, 1H), 3.98(dd, J=11.4, 6.3 Hz, 1H), 3.25—3.05(m, 1H), 2.65—2.63(m, 1H), 2.28(s, 3H) | 137.4, 134.0, 133.9, 132.2, 132.1, 129.8, 128.9, 127.7, 127.2, 126.1, 86.4, 77.4, 77.1, 76.9, 58.2, 27.9, 21.2 |
3g | 7.31—7.25(m, 7H), 6.84(d, J=8.2 Hz, 2H), 5.68(s, 1H), 3.82(s, 3H), 3.42(s, 3H) | 141.3, 139.0, 134.3, 133.2, 129.4, 128.2, 127.6, 125.2, 90.2, 58.2, 56.8 |
3h | 7.30—7.29(d, J=8.3 Hz, 4H), 7.25—7.22(m, 5H), 5.80(s, 1H), 3.82(s, 3H), 3.38(s, 3H) | 138.3, 136.0, 133.5, 132.8, 132.0, 129.3, 128.2, 127.6, 126.9, 89.2, 55.9 |
3i | 7.31—7.22(m, 7H), 7.08(d, J=8.2 Hz, 2H), 5.68(s, 1H), 3.51(m, 2H), 1.27(s, 3H), 1.26(s, 6H) | 139.6, 138.9, 133.3, 131.2, 130.8, 129.1, 128.7, 126.4, 87.9, 78.2, 23.7, 21.2 |
3j | 7.32—7.28(m, 6H), 7.24(t, J=7.5 Hz, 1H), 6.98(d, J=8.2 Hz, 2H), 5.68(s, 1H), 3.68(s, 1H), 3.47(m, 1H), 1.24(s, 3H), 1.22(s, 6H) | 142.8, 138.9, 133.3, 131.2, 130.8, 128.7, 126.4, 115.6, 87.9, 75.2, 56.0, 22.7, 21.2 |
3k | 7.32—7.28(m, 6H), 7.28—7.21(m, 3H), 5.68(s, 1H), 3.47(m, 1H), 1.24(s, 3H), 1.22(s, 6H) | 138.9, 135.5, 133.6, 132.2, 129.9, 128.9, 128.2, 126.4, 87.9, 75.2, 21.2 |
3l | 7.43—7.31(m, 5H), 7.24—7.19(m, 4H), 6.49(s, 1H), 4.55—4.53(m, 2H), 3.20—3.09(m, 1H), 2.72(dd, J=16.5, 2.4 Hz, 1H) | 136.6, 132.9, 132.5, 132.3, 132.2, 128.1, 127.9, 126.9, 126.1, 125.2, 85.1, 57.4, 25.9 |
3m | 7.62(d, J=7.8 Hz, 2H), 7.41—7.32(m, 1H), 7.26—7.00(m, 5H), 6.45(s, 1H), 4.55(m, 1H), 3.98(dd, J=11.4, 6.3 Hz, 1H), 3.25—3.05(m, 1H), 2.65(dd, J=16.5, 2.9 Hz, 1H), 2.28(s, 3H) | 138.4, 136.0, 133.5, 132.7, 132.0, 129.3, 128.2, 127.6, 126.9, 126.1, 125.2, 85.1, 57.5, 25.8 |
Table 2 1H NMR, 13C NMR data of compounds 3a—3m
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
3a | 7.17—7.26(m, 10H), 5.67(s, 1H), 3.47(s, 3H) | 139.5, 138.0, 134.3, 133.2, 129.5, 128.1, 127.9, 126.4, 90.2, 56.8 |
3b | 7.31(dd, J=4.0, 2.9 Hz, 5H), 7.23(d, J=8.2 Hz, 2H), 7.06(m, 3H), 5.68(s, 1H), 3.42(m, 2H), 1.20(t, J=7.5 Hz, 3H) | 139.4, 138.1, 135.1, 133.2, 129.5, 128.1, 128.1, 127.2, 91.3, 58.2, 21.3 |
3c | 7.32—7.30(m, 5H), 7.23(d, J=8.2 Hz, 2H), 7.03(t, J=8.2 Hz, 3H), 5.97(s, 1H), 3.53(m, 1H), 1.29(s, 3H), 1.27(s, 3H) | 138.6, 133.7, 131.4, 129.7, 129.3, 129.0, 128.2, 126.3, 85.0, 73.5, 23.9, 23.8 |
3d | 7.34—7.28(m, 5H), 7.24—7.20(m, 5H), 7.11—7.08(t, J=8.2 Hz, 2H), 6.93—6.85(m, 3H), 6.07(s, 1H) | 146.5, 139.0, 134.5, 132.5, 132.3, 130.8, 130.7, 129.4, 129.3, 128.5, 127.6, 125.4, 119.8, 89.2 |
3e | 7.97(d, J=6.1 Hz, 2H), 7.47(t, J=7.4 Hz, 1H), 7.40(t, J=7.4 Hz, 2H), 7.35—7.15(m, 10H), 7.09(t, J=7.4 Hz, 1H) | 164.2, 138.9, 133.8, 133.3, 131.4, 131.3, 130.5, 129.8, 129.7, 129.7, 129.6, 129.4, 129.3, 128.8, 128.7, 128.6, 128.4, 125.9, 125.8, 85.3 |
3f | 7.48(d, J=7.8 Hz, 2H), 7.40—7.30(m, 1H), 7.26—7.00(m, 5H), 6.45(s, 1H), 4.55—4.52(m, 1H), 3.98(dd, J=11.4, 6.3 Hz, 1H), 3.25—3.05(m, 1H), 2.65—2.63(m, 1H), 2.28(s, 3H) | 137.4, 134.0, 133.9, 132.2, 132.1, 129.8, 128.9, 127.7, 127.2, 126.1, 86.4, 77.4, 77.1, 76.9, 58.2, 27.9, 21.2 |
3g | 7.31—7.25(m, 7H), 6.84(d, J=8.2 Hz, 2H), 5.68(s, 1H), 3.82(s, 3H), 3.42(s, 3H) | 141.3, 139.0, 134.3, 133.2, 129.4, 128.2, 127.6, 125.2, 90.2, 58.2, 56.8 |
3h | 7.30—7.29(d, J=8.3 Hz, 4H), 7.25—7.22(m, 5H), 5.80(s, 1H), 3.82(s, 3H), 3.38(s, 3H) | 138.3, 136.0, 133.5, 132.8, 132.0, 129.3, 128.2, 127.6, 126.9, 89.2, 55.9 |
3i | 7.31—7.22(m, 7H), 7.08(d, J=8.2 Hz, 2H), 5.68(s, 1H), 3.51(m, 2H), 1.27(s, 3H), 1.26(s, 6H) | 139.6, 138.9, 133.3, 131.2, 130.8, 129.1, 128.7, 126.4, 87.9, 78.2, 23.7, 21.2 |
3j | 7.32—7.28(m, 6H), 7.24(t, J=7.5 Hz, 1H), 6.98(d, J=8.2 Hz, 2H), 5.68(s, 1H), 3.68(s, 1H), 3.47(m, 1H), 1.24(s, 3H), 1.22(s, 6H) | 142.8, 138.9, 133.3, 131.2, 130.8, 128.7, 126.4, 115.6, 87.9, 75.2, 56.0, 22.7, 21.2 |
3k | 7.32—7.28(m, 6H), 7.28—7.21(m, 3H), 5.68(s, 1H), 3.47(m, 1H), 1.24(s, 3H), 1.22(s, 6H) | 138.9, 135.5, 133.6, 132.2, 129.9, 128.9, 128.2, 126.4, 87.9, 75.2, 21.2 |
3l | 7.43—7.31(m, 5H), 7.24—7.19(m, 4H), 6.49(s, 1H), 4.55—4.53(m, 2H), 3.20—3.09(m, 1H), 2.72(dd, J=16.5, 2.4 Hz, 1H) | 136.6, 132.9, 132.5, 132.3, 132.2, 128.1, 127.9, 126.9, 126.1, 125.2, 85.1, 57.4, 25.9 |
3m | 7.62(d, J=7.8 Hz, 2H), 7.41—7.32(m, 1H), 7.26—7.00(m, 5H), 6.45(s, 1H), 4.55(m, 1H), 3.98(dd, J=11.4, 6.3 Hz, 1H), 3.25—3.05(m, 1H), 2.65(dd, J=16.5, 2.9 Hz, 1H), 2.28(s, 3H) | 138.4, 136.0, 133.5, 132.7, 132.0, 129.3, 128.2, 127.6, 126.9, 126.1, 125.2, 85.1, 57.5, 25.8 |
Entry | Oxidant | n(Oxidant)/mmol | T/℃ | Solvent | Yieldb(%) |
---|---|---|---|---|---|
1 | DTBP | 4.0 | 120 | Dioxane | 39 |
2 | K2S2O8 | 4.0 | 120 | Dioxane | |
3 | TBHP | 4.0 | 120 | Dioxane | 20 |
4 | DDQ | 4.0 | 120 | Dioxane | 12 |
5 | BPO | 4.0 | 120 | Dioxane | Trace |
6 | DTBP | 3.0 | 120 | Dioxane | 44 |
7 | DTBP | 2.0 | 120 | Dioxane | 53 |
8 | DTBP | 1.5 | 120 | Dioxane | 80 |
9 | DTBP | 1.0 | 120 | Dioxane | 32 |
10 | DTBP | 1.5 | 100 | Dioxane | 58 |
11 | DTBP | 1.5 | 140 | Dioxane | 67 |
12 | DTBP | 1.5 | 120 | Benzene | 69 |
13 | DTBP | 1.5 | 120 | PhCl | 56 |
14 | DTBP | 1.5 | 120 | Toluene | 13 |
Table 3 Optimization of the reactions between thiophenol and benzyl ethera
Entry | Oxidant | n(Oxidant)/mmol | T/℃ | Solvent | Yieldb(%) |
---|---|---|---|---|---|
1 | DTBP | 4.0 | 120 | Dioxane | 39 |
2 | K2S2O8 | 4.0 | 120 | Dioxane | |
3 | TBHP | 4.0 | 120 | Dioxane | 20 |
4 | DDQ | 4.0 | 120 | Dioxane | 12 |
5 | BPO | 4.0 | 120 | Dioxane | Trace |
6 | DTBP | 3.0 | 120 | Dioxane | 44 |
7 | DTBP | 2.0 | 120 | Dioxane | 53 |
8 | DTBP | 1.5 | 120 | Dioxane | 80 |
9 | DTBP | 1.0 | 120 | Dioxane | 32 |
10 | DTBP | 1.5 | 100 | Dioxane | 58 |
11 | DTBP | 1.5 | 140 | Dioxane | 67 |
12 | DTBP | 1.5 | 120 | Benzene | 69 |
13 | DTBP | 1.5 | 120 | PhCl | 56 |
14 | DTBP | 1.5 | 120 | Toluene | 13 |
Entry | Compd. | Yield(%)b | Entry | Compd. | Yield(%)b |
---|---|---|---|---|---|
1 | 79 | 7 | 82 | ||
2 | 78 | 8 | 74 | ||
3 | 82 | 9 | 86 | ||
4 | 79 | 10 | 81 | ||
5 | 77 | 11 | 76 | ||
6 | 80 | 12 | 76 |
Table 4 Scope of the reactiona
Entry | Compd. | Yield(%)b | Entry | Compd. | Yield(%)b |
---|---|---|---|---|---|
1 | 79 | 7 | 82 | ||
2 | 78 | 8 | 74 | ||
3 | 82 | 9 | 86 | ||
4 | 79 | 10 | 81 | ||
5 | 77 | 11 | 76 | ||
6 | 80 | 12 | 76 |
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