Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers†

doi:10.7503/cjcu20180599

Abstract

Abstract:

Ortho-hydroxybenzyl thioethers play a vital role in chemical biology as they have anti-oxidant and anti-inflammatory properties. o-Quinone derivatives is not only a variety of active and important intermediate, but also widely used in the synthesis of natural products and medicinal chemistry. In the present study, the Sc(Ⅲ) catalyzed nucleophilic addition to o-quinone methides by thiols for the synthesis of ortho-hydroxybenzyl thioethers was developed. The reactions could be carried out with different primary thiols, secondary thiols and benzothiols. For 2-[hydroxyl(phenyl)methyl]phenols, electron-withdrawing groups and electron-donating groups on aromatic rings could react smoothly to obtain corresponding products. The structures of the products were characterized by infrared spectra, proton nuclear magnetic resonance, carbon nuclear magnetic resonance and high resolution mass spectra. The prominent features of the present strategy are wide substrate scope, mild reaction conditions and moderate to good yields. Furthermore, the reaction could be scaled up to multigram scale. A preliminary series of control experiments has been analyzed and the study on the extension to para-hydroxybenzyl alcohols for the synthesis of para-hydroxybenzyl thioethers has been achieved.

Key words: o-Quinone, Scandium(Ⅲ);, Thiol, Nucleophilic addition, ortho-Hydroxybenzyl thioether

CLC Number:

O622.7

TrendMD:

ZHANG Shuo,YU Yitao,LI Qinggang,ZHAO Ning,HOU Zitong,LIU Yifan,LI Bing,MU Qiuhong,LI Jinhui,WANG Feng,PENG Dan. Sc(Ⅲ) Catalyzed Nucleophilic Addition of in situ Generated ortho-Quinone Methides with Thiols: an Efficient Access to ortho-Hydroxybenzyl Thioethers^†[J]. Chem. J. Chinese Universities, 2019, 40(4): 725.

Figures/Tables 6

Scheme 1 Sc(OTf)3 catalyzed nucleophilic addition reaction by thiols3a: R1=H, R2=Ph, R3=H, R=C2H5; 3b: R1=H, R2=Ph, R3=H, R=n-propyl; 3c: R1=H, R2=Ph, R3=H, R=n-pentyl; 3e: R1=H, R2=Ph, R3=H, R=heptyl; 3f: R1=H, R2=Ph, R3=H, R=isobutyl; 3g: R1=H, R2=Ph, R3=H, R=isopentyl; 3h: R1=H, R2=Ph, R3=H, R=isopropyl; 3i: R1=H, R2=Ph, R3=H, R=cyclopentyl; 3j: R1=H, R2=Ph, R3=H, R=benzyl; 3k: R1=H, R2=Ph, R3=H, R=4-(tert-butyl)benzyl; 3l: R1=H, R2=Ph, R3=H, R=4-chlorobenzyl; 3m: R1=H, R2=Ph, R3=H, R=4-methylbenzyl; 3n: R1=H, R2=Ph, R3=tert-butyl, R=C2H5; 3o: R1=H, R2=Ph, R3=ethoxy, R=C2H5; 3p: R1=CH3, R2=Ph, R3=H, R=C2H5; 3q: R1=emthoxy, R2=Ph, R3=H, R=C2H5; 3r: R1=H, R2=o-tolyl, R3=H, R=C2H5; 3s: R1=H, R2=4-chlorophenyl, R3=H, R=C2H5; 3t: R1=H, R2=3-fluorophenyl, R3=H, R=C2H5; 3u: R1=H, R2=4-fluorophenyl, R3=H, R=C2H5; 3v: R1=Cl, R2=Ph, R3=H, R=C2H5; 3w: R1=H, R2=cyclohexyl, R3=H, R=C2H5; 3x: R1=H, R2=H, R3=H, R=C2H5

Table 1 Optimization of reaction conditionsa

Entry	Catalyst	Solvent	Temperature/℃	t/h	Yield^b(%)
1	Ga(OTf)₃	DCE	50	4	0
2	In(OTf)₃	DCE	50	4	0
3	Sc(OTf)₃	DCE	50	4	92
4	Conc. HCl	DCE	50	8	56
5	H₂SO₄	DCE	50	8	52
6	AlCl₃	DCE	50	8	62
7	Sc(OTf)₃	Toluene	50	4	72
8	Sc(OTf)₃	THF	50	4	76
9	Sc(OTf)₃	DCE	50	2	92
10	Sc(OTf)₃	DCE	50	1	75
11	Sc(OTf)₃	DCE	40	6	82
12^c	Sc(OTf)₃	DCE	50	6	78
13^d	Sc(OTf)₃	DCE	50	2	93

Table 2 Appearance, yields, melting points, HRMS and IR data for compounds 3a—3x and 4a

Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3a	Colorless oil	92	245.0996	3290, 3263, 3029, 1596, 1582, 1488, 1454, 1340, 1269, 1234, 754, 699
3b	Colorless oil	90	259.1150	3289, 3062, 3029, 1596, 1582, 1487, 1454, 1339, 1270, 1236, 754, 699
3c	Colorless oil	86	273.1312	3291, 3029, 1596, 1582, 1487, 1454, 1356, 1272, 1233, 754, 699
3d	Colorless oil	84	287.1465	3292, 3029, 1596, 1582, 1487, 1454, 1341, 1271, 1234, 754, 699
3e	Colorless oil	82	315.1779	3290, 3029, 1596, 1582, 1487, 1454, 1356, 1271, 1234, 753, 699
3f	Colorless oil	87	273.1305	3291, 3029, 1597, 1583, 1488, 1454, 1366, 1271, 1234, 754, 699
3g	Colorless oil	85	287.1467	3290, 3029, 1597, 1583, 1488, 1454, 1367, 1273, 1233, 754, 699
3h^[43]	Colorless oil	88	259.1150	3290, 3029, 1598, 1583, 1489, 1454, 1366, 1271, 1235, 754, 699
3i	Colorless oil	86	285.1308	3289, 3028, 1644, 1597, 1489, 1453, 1365, 1271, 1235, 754, 699
3j^[44]	Colorless oil	91	307.1152	3289, 3028, 1644, 1599, 1493, 1454, 1341, 1272, 1234, 755, 699
3k	Colorless oil	95	363.1777	3289, 3030, 1647, 1599, 1488, 1456, 1365, 1271, 1236, 756, 701
3l	Colorless oil	86	341.0762	3296, 3029, 1644, 1597, 1490, 1454, 1365, 1272, 1233, 755, 699
Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3m	Colorless oil	92	321.1305	3288, 3027, 1645, 1596, 1486, 1454, 1353, 1271, 1235, 754, 699
3n	Colorless oil	90	301.1622	3246, 3028, 1655, 1600, 1586, 1494, 1483, 1363, 1268, 1231, 749, 701
3o	Colorless oil	82	289.1257	3525, 3028, 1662, 1614, 1598, 1471, 1452, 1372, 1271, 1220, 732, 698
3p	Colorless oil	95	259.1151	3291, 3029, 1647, 1613, 1601, 1506, 1453, 1265, 1247, 702
3q	Colorless oil	90	275.1102	3392, 3028, 1501, 1451, 1266, 1240, 701
3r	Colorless oil	88	259.1151	3287, 3020, 1644, 1601, 1485, 1269, 1240, 753
3s	Colorless oil	86	279.0604	3298, 2968, 2928, 1644, 1596, 1488, 1455, 1268, 1233, 755
3t	Colorless oil	84	263.0901	3305, 2969, 2928, 1643, 1613, 1589, 1486, 1267, 1234, 755
3u	Colorless oil	82	263.0903	3305, 2969, 2928, 1603, 1506, 1487, 1269, 1226, 755
3v	Colorless oil	90	279.0605	3294, 2969, 2928, 1642, 1599, 1482, 1416, 1268, 1234, 698
3w	Colorless oil	85	251.1464	3271, 2927, 2852, 1609, 1581, 1487, 1451, 1271, 1231, 754
3x^[45]	Colorless oil	88	169.0685	269, 2968, 2926, 1612, 1597, 1450, 1265, 1226, 699
4a^[44]	Colorless oil	85	245.0997

Table 2 Appearance, yields, melting points, HRMS and IR data for compounds 3a—3x and 4a

Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3a	Colorless oil	92	245.0996	3290, 3263, 3029, 1596, 1582, 1488, 1454, 1340, 1269, 1234, 754, 699
3b	Colorless oil	90	259.1150	3289, 3062, 3029, 1596, 1582, 1487, 1454, 1339, 1270, 1236, 754, 699
3c	Colorless oil	86	273.1312	3291, 3029, 1596, 1582, 1487, 1454, 1356, 1272, 1233, 754, 699
3d	Colorless oil	84	287.1465	3292, 3029, 1596, 1582, 1487, 1454, 1341, 1271, 1234, 754, 699
3e	Colorless oil	82	315.1779	3290, 3029, 1596, 1582, 1487, 1454, 1356, 1271, 1234, 753, 699
3f	Colorless oil	87	273.1305	3291, 3029, 1597, 1583, 1488, 1454, 1366, 1271, 1234, 754, 699
3g	Colorless oil	85	287.1467	3290, 3029, 1597, 1583, 1488, 1454, 1367, 1273, 1233, 754, 699
3h^[43]	Colorless oil	88	259.1150	3290, 3029, 1598, 1583, 1489, 1454, 1366, 1271, 1235, 754, 699
3i	Colorless oil	86	285.1308	3289, 3028, 1644, 1597, 1489, 1453, 1365, 1271, 1235, 754, 699
3j^[44]	Colorless oil	91	307.1152	3289, 3028, 1644, 1599, 1493, 1454, 1341, 1272, 1234, 755, 699
3k	Colorless oil	95	363.1777	3289, 3030, 1647, 1599, 1488, 1456, 1365, 1271, 1236, 756, 701
3l	Colorless oil	86	341.0762	3296, 3029, 1644, 1597, 1490, 1454, 1365, 1272, 1233, 755, 699
Compd.	Appearance	Yield^*(%)	HRMS, m/z [M+H]⁺	IR(film), $ν ~$ /cm^-1
3m	Colorless oil	92	321.1305	3288, 3027, 1645, 1596, 1486, 1454, 1353, 1271, 1235, 754, 699
3n	Colorless oil	90	301.1622	3246, 3028, 1655, 1600, 1586, 1494, 1483, 1363, 1268, 1231, 749, 701
3o	Colorless oil	82	289.1257	3525, 3028, 1662, 1614, 1598, 1471, 1452, 1372, 1271, 1220, 732, 698
3p	Colorless oil	95	259.1151	3291, 3029, 1647, 1613, 1601, 1506, 1453, 1265, 1247, 702
3q	Colorless oil	90	275.1102	3392, 3028, 1501, 1451, 1266, 1240, 701
3r	Colorless oil	88	259.1151	3287, 3020, 1644, 1601, 1485, 1269, 1240, 753
3s	Colorless oil	86	279.0604	3298, 2968, 2928, 1644, 1596, 1488, 1455, 1268, 1233, 755
3t	Colorless oil	84	263.0901	3305, 2969, 2928, 1643, 1613, 1589, 1486, 1267, 1234, 755
3u	Colorless oil	82	263.0903	3305, 2969, 2928, 1603, 1506, 1487, 1269, 1226, 755
3v	Colorless oil	90	279.0605	3294, 2969, 2928, 1642, 1599, 1482, 1416, 1268, 1234, 698
3w	Colorless oil	85	251.1464	3271, 2927, 2852, 1609, 1581, 1487, 1451, 1271, 1231, 754
3x^[45]	Colorless oil	88	169.0685	269, 2968, 2926, 1612, 1597, 1450, 1265, 1226, 699
4a^[44]	Colorless oil	85	245.0997

Table 3 1H NMR and 13C NMR data for compounds 3a—3x and 4a

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3a	7.40(d, J=7.4 Hz, 2H), 7.32—7.16(m, 5H), 7.05(dd, J=7.6, 1.2 Hz, 1H), 6.91(dd, J=8.0, 0.7 Hz, 1H), 6.88—6.82(m, 1H), 5.39(s, 1H), 2.49—2.43(m, 2H), 1.23(t, J=7.4 Hz, 3H)	155.15, 139.31, 130.17, 129.21, 128.69, 128.67, 128.53, 128.51, 127.55, 125.16, 120.76, 117.60, 50.47, 26.36, 14.20
3b	7.40(d, J=7.4 Hz, 2H), 7.34—7.29(m, 2H), 7.21(ddd, J=15.4, 10.6, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.95—6.89(m, 1H), 6.84(td, J=7.6, 1.0 Hz, 1H), 5.35(s, 1H), 2.48—2.39(m, 2H), 1.61(dd, J=14.6, 7.3 Hz, 2H), 0.95(t, J=7.4 Hz, 3H)	155.22, 139.30, 130.18, 129.21, 128.66, 128.48, 127.53, 125.11, 120.70, 117.64, 50.97, 34.33, 22.32, 13.49
3c	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=10.0, 4.8 Hz, 3H), 7.26—7.11(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.90(m, 1H), 6.88—6.82(m, 1H), 5.35(s, 1H), 2.49—2.42(m, 2H), 1.63—1.51(m, 2H), 1.38—1.33(m, 2H), 0.85(t, J=7.3 Hz, 3H)	155.23, 139.29, 130.19, 129.21, 128.67, 128.51, 128.49, 128.46, 127.54, 125.11, 120.71, 117.64, 51.04, 32.02, 21.01, 21.96, 13.64
3d	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=9.7, 5.1 Hz, 3H), 7.28—7.13(m, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.96—6.88(m, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.45(tq, J=10.7, 5.3 Hz, 2H), 1.57(dd, J=14.7, 7.3 Hz, 2H), 1.31—1.26(m, 4H), 0.85(t, J=7.1 Hz, 3H)	155.23, 139.31, 130.19, 129.21, 128.67, 128.51, 128.48, 128.46, 127.53, 125.12, 120.71, 117.63, 51.05, 32.33, 30.99, 28.61, 22.23, 13.94
3e	7.40(d, J=7.5 Hz, 2H), 7.31(dd, J=9.9, 4.9 Hz, 3H), 7.27—7.17(m, 2H), 7.03(dd, J=7.6, 1.2 Hz, 1H), 6.92(dd, J=8.0, 0.6 Hz, 1H), 6.86—6.82(m, 1H), 5.34(s, 1H), 2.45(tq, J=10.8, 5.3 Hz, 2H), 1.60—1.56(m, 2H), 1.32—1.23(m, 8H), 0.86(t, J=6.9 Hz, 3H)	155.25, 139.29, 130.18, 129.21, 128.66, 128.54, 128.49, 127.53, 125.09, 120.70, 117.65, 51.08, 32.34, 31.67, 28.92, 28.80, 28.77, 22.61, 14.09
3f	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=13.8, 6.6 Hz, 3H), 7.21(ddd, J=11.3, 8.7, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.92(dd, J= 8.0, 0.6 Hz, 1H), 6.87—6.80(m, 1H), 5.31(s, 1H), 2.35(qd, J=12.5, 6.8 Hz, 2H), 1.83(dt, J=13.4, 6.7 Hz, 1H), 0.95(dd, J=8.0, 6.8 Hz, 6H)	155.26, 139.36, 130.24, 129.22, 128.66, 128.51, 128.48, 128.45, 127.54, 125.12, 120.69, 117.65, 51.54, 41.27, 28.24, 22.22, 21.98
3g	7.40(d, J=7.4 Hz, 2H), 7.36—7.26(m, 3H), 7.21(ddd, J=17.1, 11.2, 4.3 Hz, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.92(d, J=7.7 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.48—2.43(m, 2H), 1.61(dt, J=13.3, 6.6 Hz, 1H), 1.50—1.45(m, 2H), 0.84—0.81(m, 6H)	155.22, 139.26, 130.19, 129.23, 128.66, 128.51, 128.49, 128.46, 127.54, 125.06, 120.71, 117.64, 51.03, 37.92, 30.36, 27.40, 22.32, 22.15
3h	7.49—7.34(m, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.14(m, 2H), 7.04(dd, J=7.6, 1.2 Hz, 1H), 6.92(d, J=8.0 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.41(s, 1H), 2.77(dt, J=13.4, 6.7 Hz, 1H), 1.29—1.24(m, 6H)	155.30, 139.28, 130.09, 129.19, 128.67, 128.48, 127.50, 125.11, 120.73, 117.73, 50.13, 35.76, 23.07, 22.85
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3i	7.40(d, J=7.3 Hz, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.13(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.88(m, 1H), 6.85(dd, J=10.8, 4.1 Hz, 1H), 5.36(s, 1H), 2.91(p, J=7.0 Hz, 1H), 1.91(dt, J=12.3, 6.3 Hz, 2H), 1.72—1.70(m, 2H), 1.64—1.50(m, 4H)	155.33, 139.37, 130.05, 129.15, 128.64, 128.46, 128.44, 127.47, 125.36, 120.70, 117.71, 51.40, 44.23, 33.65, 33.20, 24.88, 24.74
3j	7.36(d, J=7.3 Hz, 2H), 7.30(t, J=7.3 Hz, 4H), 7.27—7.22(m, 2H), 7.18(dd, J=12.7, 4.5 Hz, 3H), 6.95(dd, J=7.7, 1.3 Hz, 1H), 6.90(d, J= 8.4 Hz, 2H), 6.86—6.79(m, 1H), 5.11(s, 1H), 3.59(d, J=3.2 Hz, 2H)	155.03, 138.75, 137.28, 130.31 , 129.30, 129.01, 128.99, 128.76, 128.73, 127.65, 127.47, 124.86, 120.80, 117.60, 49.68, 36.54
3k	7.34(dt, J=14.9, 7.8 Hz, 6H), 7.27—7.19(m, 2H), 7.15(d, J=8.2 Hz, 2H), 6.99(s, 1H), 6.96—6.90(m, 2H), 6.88—6.79(m, 1H), 5.14(s, 1H), 3.59(d, J=2.5 Hz, 2H), 1.32(s, 9H)	155.14, 150.39, 138.73, 134.04, 130.35, 129.27, 128.73, 128.67, 128.64, 127.59, 125.59, 124.78, 120.70, 117.64, 49.97, 36.13, 34.57, 31.37
3l	7.36—7.18(m, 8H), 7.11(d, J=8.4 Hz, 2H), 6.99(dd, J=7.6, 1.3 Hz, 1H), 6.93—6.81(m, 2H), 6.78(s, 1H), 5.12(s, 1H), 3.56(s, 2H)	154.87, 138.61, 135.81, 133.18, 130.32, 130.29, 129.35,128.81, 128.75, 128.64, 127.70, 124.63, 120.88, 117.52, 49.65, 35.89
3m	7.40—7.29(m, 4H), 7.26—7.17(m, 2H), 7.13—7.08(m, 4H), 6.96(s, 1H), 6.93—6.90(m, 2H), 6.83(t, J=7.4 Hz, 1H), 5.09(s, 1H), 3.56(d, J=5.1 Hz, 2H), 2.33(s, 3H)	155.08, 138.74, 137.14, 134.11, 130.31, 129.41, 129.26 , 128.90, 128.79, 128.71, 127.61, 124.87, 120.74, 117.62, 49.64, 36.21, 21.20
3n	7.61(s, 1H), 7.42(d, J=7.4 Hz, 2H), 7.34(t, J=7.4 Hz, 2H), 7.30—7.21(m, 2H), 6.74(dd, J=7.2, 5.3 Hz, 2H), 5.35(s, 1H), 2.46(q, J=7.4 Hz, 2H), 1.44(s, 9H), 1.25(t, J=7.3 Hz, 3H)	154.38, 138.88, 138.29, 128.82, 128.63, 128.04, 127.56, 126.66, 125.19, 119.80, 77.36, 77.05, 76.73, 51.54, 34.93, 29.76, 26.27, 14.24
3o	7.47(d, J=7.4 Hz, 2H), 7.28(t, J=7.5 Hz, 2H), 7.22—7.08(m, 2H), 6.81(t, J=8.0 Hz, 1H), 6.71(dd, J=8.0, 1.1 Hz, 1H), 5.98(s, 1H), 5.66(s, 1H), 4.10—4.02(m, 2H), 2.44(q, J=7.4 Hz, 2H), 1.41(t, J=7.0 Hz, 3H), 1.23(t, J=7.4 Hz, 3H)	145.71, 143.18, 141.48, 128.38, 128.35, 127.33, 126.88, 121.02, 119.63, 110.09, 64.57, 46.17, 26.31, 14.92, 14.31
3p	7.40(d, J=7.5 Hz, 2H), 7.31(t, J=7.4 Hz, 2H), 7.26—7.22(m, 1H), 7.12(s, 1H), 7.00(dd, J=8.2, 1.7 Hz, 1H), 6.83(dd, J=8.1, 4.9 Hz, 2H), 5.34(s, 1H), 2.48(dd, J=7.4, 4.0 Hz, 2H), 2.21(s, 3H), 1.25(t, J=7.4 Hz, 3H)	152.92, 139.33, 130.56, 129.85, 129.72, 128.65, 128.45, 127.48, 124.56, 117.49, 50.76, 26.36, 20.57, 14.16
3q	7.41(d, J=7.4 Hz, 2H), 7.32(dd, J=10.1, 4.7 Hz, 2H), 7.25(t, J=7.2 Hz, 1H), 6.86(d, J=8.8 Hz, 1H), 6.76(dd, J=8.8, 3.1 Hz, 2H), 6.63(d, J=3.0 Hz, 1H), 5.34(s, 1H), 3.70(s, 3H), 2.48(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	153.54, 148.85, 139.05, 128.66, 128.64, 128.49, 128.44, 127.56, 126.25, 118.26, 115.74, 113.95, 55.66, 50.59, 26.35, 14.18
3r	7.54—7.51(m, 1H), 7.29(s, 1H), 7.23—7.11(m, 4H), 6.94(ddd, J=11.9, 7.9, 1.0 Hz, 2H), 6.83—6.80(m, 1H), 5.52(s, 1H), 2.51(q, J=7.4 Hz, 2H), 2.39(s, 3H), 1.27(t, J=7.4 Hz, 3H)	155.18, 137.18, 136.28, 130.73, 129.94, 128.98, 128.62, 127.48, 126.47, 125.15, 120.79, 117.44, 46.90, 26.47, 19.31, 14.16
3s	7.34(d, J=8.5 Hz, 2H), 7.22(ddd, J=11.3, 8.7 Hz, 4.7 Hz, 2H), 7.08—7.03(m, 2H), 6.93—6.85(m, 2H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	154.95, 137.91, 133.29, 129.97, 129.84, 129.35, 128.78, 124.75, 120.86, 117.63, 49.68, 26.37, 14.12
3t	7.30—7.26(m, 1H), 7.21(ddd, J=12.9, 9.8, 4.7 Hz, 2H), 7.14(dd, J=10.1, 2.0 Hz, 1H), 7.06(dd, J=7.6, 1.3 Hz, 1H), 7.01(s, 1H), 6.97—6.86(m, 3H), 5.38(s, 1H), 2.49(qd, J=7.4, 1.6 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	164.17, 161.72, 154.88, 142.07(d, J=6.9 Hz), 130.07(d, J=8.3 Hz), 129.99, 129.37, 124.76, 124.12(d, J=2.8 Hz), 120.89, 117.58, 115.63, 115.41, 114.56, 114.35, 49.70, 26.36, 14.12
3u	7.39—7.35(m, 2H), 7.22(td, J=8.1, 1.6 Hz, 1H), 7.17(s, 1H), 7.05—6.98(m, 3H), 6.93(dd, J =8.0, 0.8 Hz, 1H), 6.87(td, J=7.5, 1.0 Hz, 1H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.7 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	162.04(d, J=245 Hz), 155.05, 134.99(d, J=3 Hz), 130.12, 130.03(d, J=2.6 Hz), 129.32, 124.87, 120.80, 117.69, 115.59, 115.38, 49.78, 26.35, 14.10
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3v	7.40—7.25(m, 6H), 7.16(dd, J=8.6, 2.6 Hz, 1H), 7.03(d, J=2.5 Hz, 1H), 6.86(d, J=8.6 Hz, 1H), 5.31(s, 1H), 2.49(dd, J=13.7, 7.0 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	153.82, 138.45, 129.70, 129.03, 128.80, 128.76, 128.41, 128.36, 128.32, 127.82, 126.81, 125.44, 119.00, 50.32, 29.71, 26.41, 14.10
3w	7.64(s, 1H), 7.18—7.14(m, 1H), 6.96(dd, J=7.5, 1.3 Hz, 1H), 6.86(d, J=7.7, 1H), 6.80(dd, J=11.5, 4.1 Hz, 1H), 3.78(d, J=9.1 Hz, 1H), 2.29(qd, J=7.4, 1.5 Hz, 2H), 2.14(d, J=12.8 Hz, 1H), 1.87—1.85(m, 1H), 1.74(dd, J=10.4, 2.7 Hz, 1H), 1.63—1.60(m, 2H), 1.41(d, J=13.0 Hz, 1H), 1.23(ddd, J=15.7, 8.6, 5.2 Hz, 1H), 1.15—1.03(m, 6H), 0.92—0.90(m, 1H)	155.51, 131.14, 128.68, 124.72, 119.88, 117.59, 55.16, 41.45, 32.07, 32.02, 26.28, 26.16, 14.24
3x	7.20(t, J=7.5 Hz, 1H), 7.08(d, J=7.2 Hz, 1H), 6.97—6.79(m, 2H), 6.75(s, 1H), 3.82(s, 2H), 2.42(q, J=7.3 Hz, 2H), 1.26—1.21(m, 3H)	155.51, 130.45, 129.11, 122.44, 120.52, 117.20, 32.38 , 24.76, 14.23
4a	7.40(d, J=7.4 Hz, 2H), 7.25(td, J=17.2, 7.3 Hz, 5H), 6.74(d, J=8.5 Hz, 2H), 5.79(s, 1H), 5.12(s, 1H), 2.37(q, J=7.4 Hz, 2H), 1.19(t, J=7.4 Hz, 3H)	154.72, 141.81, 133.61, 129.56, 128.56, 128.26, 127.09, 115.49, 53.17, 26.27, 14.25

Table 3 1H NMR and 13C NMR data for compounds 3a—3x and 4a

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3a	7.40(d, J=7.4 Hz, 2H), 7.32—7.16(m, 5H), 7.05(dd, J=7.6, 1.2 Hz, 1H), 6.91(dd, J=8.0, 0.7 Hz, 1H), 6.88—6.82(m, 1H), 5.39(s, 1H), 2.49—2.43(m, 2H), 1.23(t, J=7.4 Hz, 3H)	155.15, 139.31, 130.17, 129.21, 128.69, 128.67, 128.53, 128.51, 127.55, 125.16, 120.76, 117.60, 50.47, 26.36, 14.20
3b	7.40(d, J=7.4 Hz, 2H), 7.34—7.29(m, 2H), 7.21(ddd, J=15.4, 10.6, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.95—6.89(m, 1H), 6.84(td, J=7.6, 1.0 Hz, 1H), 5.35(s, 1H), 2.48—2.39(m, 2H), 1.61(dd, J=14.6, 7.3 Hz, 2H), 0.95(t, J=7.4 Hz, 3H)	155.22, 139.30, 130.18, 129.21, 128.66, 128.48, 127.53, 125.11, 120.70, 117.64, 50.97, 34.33, 22.32, 13.49
3c	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=10.0, 4.8 Hz, 3H), 7.26—7.11(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.90(m, 1H), 6.88—6.82(m, 1H), 5.35(s, 1H), 2.49—2.42(m, 2H), 1.63—1.51(m, 2H), 1.38—1.33(m, 2H), 0.85(t, J=7.3 Hz, 3H)	155.23, 139.29, 130.19, 129.21, 128.67, 128.51, 128.49, 128.46, 127.54, 125.11, 120.71, 117.64, 51.04, 32.02, 21.01, 21.96, 13.64
3d	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=9.7, 5.1 Hz, 3H), 7.28—7.13(m, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.96—6.88(m, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.45(tq, J=10.7, 5.3 Hz, 2H), 1.57(dd, J=14.7, 7.3 Hz, 2H), 1.31—1.26(m, 4H), 0.85(t, J=7.1 Hz, 3H)	155.23, 139.31, 130.19, 129.21, 128.67, 128.51, 128.48, 128.46, 127.53, 125.12, 120.71, 117.63, 51.05, 32.33, 30.99, 28.61, 22.23, 13.94
3e	7.40(d, J=7.5 Hz, 2H), 7.31(dd, J=9.9, 4.9 Hz, 3H), 7.27—7.17(m, 2H), 7.03(dd, J=7.6, 1.2 Hz, 1H), 6.92(dd, J=8.0, 0.6 Hz, 1H), 6.86—6.82(m, 1H), 5.34(s, 1H), 2.45(tq, J=10.8, 5.3 Hz, 2H), 1.60—1.56(m, 2H), 1.32—1.23(m, 8H), 0.86(t, J=6.9 Hz, 3H)	155.25, 139.29, 130.18, 129.21, 128.66, 128.54, 128.49, 127.53, 125.09, 120.70, 117.65, 51.08, 32.34, 31.67, 28.92, 28.80, 28.77, 22.61, 14.09
3f	7.40(d, J=7.4 Hz, 2H), 7.31(dd, J=13.8, 6.6 Hz, 3H), 7.21(ddd, J=11.3, 8.7, 4.4 Hz, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.92(dd, J= 8.0, 0.6 Hz, 1H), 6.87—6.80(m, 1H), 5.31(s, 1H), 2.35(qd, J=12.5, 6.8 Hz, 2H), 1.83(dt, J=13.4, 6.7 Hz, 1H), 0.95(dd, J=8.0, 6.8 Hz, 6H)	155.26, 139.36, 130.24, 129.22, 128.66, 128.51, 128.48, 128.45, 127.54, 125.12, 120.69, 117.65, 51.54, 41.27, 28.24, 22.22, 21.98
3g	7.40(d, J=7.4 Hz, 2H), 7.36—7.26(m, 3H), 7.21(ddd, J=17.1, 11.2, 4.3 Hz, 2H), 7.03(dd, J=7.6, 1.1 Hz, 1H), 6.92(d, J=7.7 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.35(s, 1H), 2.48—2.43(m, 2H), 1.61(dt, J=13.3, 6.6 Hz, 1H), 1.50—1.45(m, 2H), 0.84—0.81(m, 6H)	155.22, 139.26, 130.19, 129.23, 128.66, 128.51, 128.49, 128.46, 127.54, 125.06, 120.71, 117.64, 51.03, 37.92, 30.36, 27.40, 22.32, 22.15
3h	7.49—7.34(m, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.14(m, 2H), 7.04(dd, J=7.6, 1.2 Hz, 1H), 6.92(d, J=8.0 Hz, 1H), 6.84(t, J=7.5 Hz, 1H), 5.41(s, 1H), 2.77(dt, J=13.4, 6.7 Hz, 1H), 1.29—1.24(m, 6H)	155.30, 139.28, 130.09, 129.19, 128.67, 128.48, 127.50, 125.11, 120.73, 117.73, 50.13, 35.76, 23.07, 22.85
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3i	7.40(d, J=7.3 Hz, 3H), 7.30(t, J=7.4 Hz, 2H), 7.26—7.13(m, 2H), 7.03(dd, J=7.6, 1.3 Hz, 1H), 6.97—6.88(m, 1H), 6.85(dd, J=10.8, 4.1 Hz, 1H), 5.36(s, 1H), 2.91(p, J=7.0 Hz, 1H), 1.91(dt, J=12.3, 6.3 Hz, 2H), 1.72—1.70(m, 2H), 1.64—1.50(m, 4H)	155.33, 139.37, 130.05, 129.15, 128.64, 128.46, 128.44, 127.47, 125.36, 120.70, 117.71, 51.40, 44.23, 33.65, 33.20, 24.88, 24.74
3j	7.36(d, J=7.3 Hz, 2H), 7.30(t, J=7.3 Hz, 4H), 7.27—7.22(m, 2H), 7.18(dd, J=12.7, 4.5 Hz, 3H), 6.95(dd, J=7.7, 1.3 Hz, 1H), 6.90(d, J= 8.4 Hz, 2H), 6.86—6.79(m, 1H), 5.11(s, 1H), 3.59(d, J=3.2 Hz, 2H)	155.03, 138.75, 137.28, 130.31 , 129.30, 129.01, 128.99, 128.76, 128.73, 127.65, 127.47, 124.86, 120.80, 117.60, 49.68, 36.54
3k	7.34(dt, J=14.9, 7.8 Hz, 6H), 7.27—7.19(m, 2H), 7.15(d, J=8.2 Hz, 2H), 6.99(s, 1H), 6.96—6.90(m, 2H), 6.88—6.79(m, 1H), 5.14(s, 1H), 3.59(d, J=2.5 Hz, 2H), 1.32(s, 9H)	155.14, 150.39, 138.73, 134.04, 130.35, 129.27, 128.73, 128.67, 128.64, 127.59, 125.59, 124.78, 120.70, 117.64, 49.97, 36.13, 34.57, 31.37
3l	7.36—7.18(m, 8H), 7.11(d, J=8.4 Hz, 2H), 6.99(dd, J=7.6, 1.3 Hz, 1H), 6.93—6.81(m, 2H), 6.78(s, 1H), 5.12(s, 1H), 3.56(s, 2H)	154.87, 138.61, 135.81, 133.18, 130.32, 130.29, 129.35,128.81, 128.75, 128.64, 127.70, 124.63, 120.88, 117.52, 49.65, 35.89
3m	7.40—7.29(m, 4H), 7.26—7.17(m, 2H), 7.13—7.08(m, 4H), 6.96(s, 1H), 6.93—6.90(m, 2H), 6.83(t, J=7.4 Hz, 1H), 5.09(s, 1H), 3.56(d, J=5.1 Hz, 2H), 2.33(s, 3H)	155.08, 138.74, 137.14, 134.11, 130.31, 129.41, 129.26 , 128.90, 128.79, 128.71, 127.61, 124.87, 120.74, 117.62, 49.64, 36.21, 21.20
3n	7.61(s, 1H), 7.42(d, J=7.4 Hz, 2H), 7.34(t, J=7.4 Hz, 2H), 7.30—7.21(m, 2H), 6.74(dd, J=7.2, 5.3 Hz, 2H), 5.35(s, 1H), 2.46(q, J=7.4 Hz, 2H), 1.44(s, 9H), 1.25(t, J=7.3 Hz, 3H)	154.38, 138.88, 138.29, 128.82, 128.63, 128.04, 127.56, 126.66, 125.19, 119.80, 77.36, 77.05, 76.73, 51.54, 34.93, 29.76, 26.27, 14.24
3o	7.47(d, J=7.4 Hz, 2H), 7.28(t, J=7.5 Hz, 2H), 7.22—7.08(m, 2H), 6.81(t, J=8.0 Hz, 1H), 6.71(dd, J=8.0, 1.1 Hz, 1H), 5.98(s, 1H), 5.66(s, 1H), 4.10—4.02(m, 2H), 2.44(q, J=7.4 Hz, 2H), 1.41(t, J=7.0 Hz, 3H), 1.23(t, J=7.4 Hz, 3H)	145.71, 143.18, 141.48, 128.38, 128.35, 127.33, 126.88, 121.02, 119.63, 110.09, 64.57, 46.17, 26.31, 14.92, 14.31
3p	7.40(d, J=7.5 Hz, 2H), 7.31(t, J=7.4 Hz, 2H), 7.26—7.22(m, 1H), 7.12(s, 1H), 7.00(dd, J=8.2, 1.7 Hz, 1H), 6.83(dd, J=8.1, 4.9 Hz, 2H), 5.34(s, 1H), 2.48(dd, J=7.4, 4.0 Hz, 2H), 2.21(s, 3H), 1.25(t, J=7.4 Hz, 3H)	152.92, 139.33, 130.56, 129.85, 129.72, 128.65, 128.45, 127.48, 124.56, 117.49, 50.76, 26.36, 20.57, 14.16
3q	7.41(d, J=7.4 Hz, 2H), 7.32(dd, J=10.1, 4.7 Hz, 2H), 7.25(t, J=7.2 Hz, 1H), 6.86(d, J=8.8 Hz, 1H), 6.76(dd, J=8.8, 3.1 Hz, 2H), 6.63(d, J=3.0 Hz, 1H), 5.34(s, 1H), 3.70(s, 3H), 2.48(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	153.54, 148.85, 139.05, 128.66, 128.64, 128.49, 128.44, 127.56, 126.25, 118.26, 115.74, 113.95, 55.66, 50.59, 26.35, 14.18
3r	7.54—7.51(m, 1H), 7.29(s, 1H), 7.23—7.11(m, 4H), 6.94(ddd, J=11.9, 7.9, 1.0 Hz, 2H), 6.83—6.80(m, 1H), 5.52(s, 1H), 2.51(q, J=7.4 Hz, 2H), 2.39(s, 3H), 1.27(t, J=7.4 Hz, 3H)	155.18, 137.18, 136.28, 130.73, 129.94, 128.98, 128.62, 127.48, 126.47, 125.15, 120.79, 117.44, 46.90, 26.47, 19.31, 14.16
3s	7.34(d, J=8.5 Hz, 2H), 7.22(ddd, J=11.3, 8.7 Hz, 4.7 Hz, 2H), 7.08—7.03(m, 2H), 6.93—6.85(m, 2H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.0 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	154.95, 137.91, 133.29, 129.97, 129.84, 129.35, 128.78, 124.75, 120.86, 117.63, 49.68, 26.37, 14.12
3t	7.30—7.26(m, 1H), 7.21(ddd, J=12.9, 9.8, 4.7 Hz, 2H), 7.14(dd, J=10.1, 2.0 Hz, 1H), 7.06(dd, J=7.6, 1.3 Hz, 1H), 7.01(s, 1H), 6.97—6.86(m, 3H), 5.38(s, 1H), 2.49(qd, J=7.4, 1.6 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	164.17, 161.72, 154.88, 142.07(d, J=6.9 Hz), 130.07(d, J=8.3 Hz), 129.99, 129.37, 124.76, 124.12(d, J=2.8 Hz), 120.89, 117.58, 115.63, 115.41, 114.56, 114.35, 49.70, 26.36, 14.12
3u	7.39—7.35(m, 2H), 7.22(td, J=8.1, 1.6 Hz, 1H), 7.17(s, 1H), 7.05—6.98(m, 3H), 6.93(dd, J =8.0, 0.8 Hz, 1H), 6.87(td, J=7.5, 1.0 Hz, 1H), 5.36(s, 1H), 2.47(qd, J=7.4, 2.7 Hz, 2H), 1.25(t, J=7.4 Hz, 3H)	162.04(d, J=245 Hz), 155.05, 134.99(d, J=3 Hz), 130.12, 130.03(d, J=2.6 Hz), 129.32, 124.87, 120.80, 117.69, 115.59, 115.38, 49.78, 26.35, 14.10
Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(CDCl₃, 100 MHz), δ
3v	7.40—7.25(m, 6H), 7.16(dd, J=8.6, 2.6 Hz, 1H), 7.03(d, J=2.5 Hz, 1H), 6.86(d, J=8.6 Hz, 1H), 5.31(s, 1H), 2.49(dd, J=13.7, 7.0 Hz, 2H), 1.26(t, J=7.4 Hz, 3H)	153.82, 138.45, 129.70, 129.03, 128.80, 128.76, 128.41, 128.36, 128.32, 127.82, 126.81, 125.44, 119.00, 50.32, 29.71, 26.41, 14.10
3w	7.64(s, 1H), 7.18—7.14(m, 1H), 6.96(dd, J=7.5, 1.3 Hz, 1H), 6.86(d, J=7.7, 1H), 6.80(dd, J=11.5, 4.1 Hz, 1H), 3.78(d, J=9.1 Hz, 1H), 2.29(qd, J=7.4, 1.5 Hz, 2H), 2.14(d, J=12.8 Hz, 1H), 1.87—1.85(m, 1H), 1.74(dd, J=10.4, 2.7 Hz, 1H), 1.63—1.60(m, 2H), 1.41(d, J=13.0 Hz, 1H), 1.23(ddd, J=15.7, 8.6, 5.2 Hz, 1H), 1.15—1.03(m, 6H), 0.92—0.90(m, 1H)	155.51, 131.14, 128.68, 124.72, 119.88, 117.59, 55.16, 41.45, 32.07, 32.02, 26.28, 26.16, 14.24
3x	7.20(t, J=7.5 Hz, 1H), 7.08(d, J=7.2 Hz, 1H), 6.97—6.79(m, 2H), 6.75(s, 1H), 3.82(s, 2H), 2.42(q, J=7.3 Hz, 2H), 1.26—1.21(m, 3H)	155.51, 130.45, 129.11, 122.44, 120.52, 117.20, 32.38 , 24.76, 14.23
4a	7.40(d, J=7.4 Hz, 2H), 7.25(td, J=17.2, 7.3 Hz, 5H), 6.74(d, J=8.5 Hz, 2H), 5.79(s, 1H), 5.12(s, 1H), 2.37(q, J=7.4 Hz, 2H), 1.19(t, J=7.4 Hz, 3H)	154.72, 141.81, 133.61, 129.56, 128.56, 128.26, 127.09, 115.49, 53.17, 26.27, 14.25

Scheme 2 Proposed reaction mechanism

Scheme 3 Reaction of 4-[hydroxy(phenyl)methyl]-phenol with CH3CH2SH

References 45

[1]	Kondo T., Mitsudo T. A., Chem.Rev., 2000, 100(8), 3205—3220
[2]	Feng M., Tang B., Liang S. H., Jiang X., Curr. Top. Med.Chem.,2016, 16(17), 1200—1216
[3]	Ilardi E. A., Vitaku E., Najardarson J. T., J. Med.Chem., 2014, 57(7), 2832—2842
[4]	Smith B. R., Eastman C. M., Nijardarson., J. Med.Chem., 2014, 57(23), 9764—9773
[5]	Wei Y. Z., Tan X. Z., Chem. Res. Chinese Universities,2017, 33(5), 731—735
[6]	Zhong S. M., Zheng M., Pu S. X., Xing Y. B., Li K. Z., Wang H., Chem. Res. Chinese Universities,2017, 33(6), 979—985
[7]	Cinar M. E., Ozturk T., Chem.Rev., 2015, 115(9), 3036—3140
[8]	Takimiya K., Osaka I., Mori T., Nakano M., Acc. Chem.Res., 2014, 47(5), 1493—1502
[9]	Scott K. A., Njardarson J. T., Top. Curr.Chem., 2018, 376, 5—38
[10]	Hammond M. L., Zambias R. A., Chang M. N., Jensen N. P., McDonald J., Thompson K., Boulton D. A., Kopka I. K., Hand K. M., Opas E. E., Luell S., Bach T., Davies P., MacIntyre D. E., Bonney R. J., Humes J. L., J. Med.Chem.,1990, 33(3), 908—918
[11]	Katritzky A. R., Zhang Z., Lan X., Lang H., J. Org.Chem., 1994, 59(7), 1900—1903
[12]	Modica E., Zanaletti R., Freccero M., Mella M., J. Org.Chem.,2001, 66(1), 41—52
[13]	Shaikh A. K., Cobb A. J. A., Varvounis G., Org.Lett., 2012, 14(2), 584—587
[14]	Lau C. K., Williams H. W. R., Tardiff S., Dufresne C., Scheigetz J., Belanger P., Can. J.Chem., 1989, 67, 1384—1387
[15]	Guo W., Wu B., Zhou X., Chen P., Wang X., Zhou Y. G., Liu Y., Li C., Angew. Chem. Int.Ed., 2015, 54(15), 4522—4526
[16]	Guo W., Wu B., Zhou X., Chen P., Wang X., Zhou Y. G., Liu Y., Li C.,Angew. Chem. Int.Ed., 2015, 54(15), 4605—4609
[17]	Lai Z., Sun J., Synlett.,2016, 27(4), 555—558
[18]	Pathak T. P., Sigman M. S., J. Org.Chem.,2011, 76(22), 9210—9215
[19]	Will N. J., Bray C. D., Chem. Eur.J.,2012, 18(30), 9160—9173
[20]	Caruana L., Fochi M., Bernardi L., Molecules,2015, 20(7), 11733—11764
[21]	Wang Z., Sun J., Synthesis,2015, 47(23), 3629—3644
[22]	Water R. W. V. D., Pettus T. R. R., Tetrahedron,2002, 58(27), 5367—5405
[23]	Kulikov A., Arumugam S., Popik V. V., J. Org.Chem.,2008, 73(19), 7611—7615
[24]	Mattson A. E., Scheidt K. A., J. Am. Chem.Soc.,2007, 129(15), 4508—4509
[25]	Luan Y., Schaus S. E., J. Am. Chem.Soc., 2012, 134(49), 19965—19968
[26]	Chen M. W., Gao L. L., Ye Z. S., Jiang G. F., Zhou Y. G., Chem.Commun.,2013, 49, 1660—1662
[27]	Bai W. J., David J. G., Feng Z. G., Weaver M. G., Wu K. L., Pettus T. R. R., Acc. Chem.Res., 2014, 47(12), 3655—3664
[28]	Zhao W., Wang Z., Chu B., Sun J., Angew. Chem. Int.Ed., 2015, 54(6), 1910—1913
[29]	Huang Y., Hayashi T., J. Am. Chem.Soc.,2015, 137(24), 7556—7559
[30]	Wan Z., Ai F., Wang Z., Zhao W., Zhu G., Lin Z., Sun J., J. Am. Chem.Soc., 2015, 137(1), 383—389
[31]	Wu B., Yu Z., Gao X., Lan Y., Zhou Y. G., Angew. Chem. Int.Ed.,2017, 56(14), 4006—4010
[32]	Chen P., Wang K., Guo W., Liu X., Liu Y., Li C., Angew. Chem. Int.Ed.,2017, 56(13), 3689—3693
[33]	Nising C. F., Brase S., Chem. Soc.Rev., 2008, 37, 1218—1228
[34]	Nising C. F., Brase S., Chem. Soc.Rev., 2012, 41, 988—999
[35]	Heravi M. M., Hajiabbasi P., Mol.Diversity,2014, 18(2), 411—439
[36]	Thirupathi N., Tung C. H., Xu Z. H.,Adv. Synth.Catal., 2018, 360(18), 3585—3589
[37]	Corma A., Gonzalez-Arellano C., Iglesias M., Sanchez F., App. Catal. A:Gen.,2010, 375(1), 49—54
[38]	Lee W. Z., Tseng H. S., Wang T. L., Tsai H. L., Kuo T. S.,Organometallics,2010, 29(13), 2874—2881
[39]	Badoiu A., Bernardinelli G., Besnard C., Kundig E. P., Org. Biomol.Chem., 2010, 8, 193—200
[40]	O’Byrne A., Murray C., Keegan D., Palacio C., Evans P., Morgan B. S., Org. Biomol.Chem., 2010, 8, 539—545
[41]	Firouzabadi H., Iranpoor N., Abbasi M., Adv. Synth.Catal., 2009, 351, 755—766
[42]	Rajabi F., Razavi S., Luque R., Green Chem.,2010, 12, 786—789
[43]	Inoue T., Inoue S., Sato K., Bull. Chem. Soc.Jpn.,1990, 63(4), 1062—1068
[44]	Lanzi M., Merad J., Boyarskaya D V., Maestri G., Allain C., Masson Géraldine., Org.Lett., 2018, 20(17), 5247—5250
[45]	Basha R. S., Chen C. W., Reddy D. M., Lee C. F., Chem-Asian J.,2018,13(17), 2475—2483