Microwave Assisted Rhodium-catalyzed C—H Activation/cyclization of Diaryl Phosphoramides and Alkynes †

doi:10.7503/cjcu20190571

Abstract

Abstract:

A microwave assisted rhodium-catalyzed C—H activation/cyclization of diaryl phosphoramides and alkynes has been developed, and a series of cyclic phosphoramides bearing five fluoro groups could be obtained in moderate to good yields. The optimized reaction conditions were established by examination of solvents, temperature, reaction time and bases. This reaction system was also feasible in a gram-scale reaction without significant decrease in the product yields, and a possible reaction mechanism was then proposed. Moreover, this methology was successfully applied to the synthesis of the novel diamine with the core of fluorine-containing substituted cyclic phosphoramide.

Key words: Microwave, [RhCp ^*Cl₂]₂, C—H activation/cyclization;, Diaryl phosphoramide

CLC Number:

O626.1

TrendMD:

ZHOU Chunni, ZHENG Ziang, PENG Wangming, WANG Hongbo, ZHANG Yumin, WANG Liang, XIAO Biao. Microwave Assisted Rhodium-catalyzed C—H Activation/cyclization of Diaryl Phosphoramides and Alkynes ^†[J]. Chem. J. Chinese Universities, 2020, 41(4): 726.

Figures/Tables 5

Scheme 1 C—H activation/cyclization of diaryl phosphoramides and alkynes

Compd.	R¹	R²		Appearance		Yield^a(%)	m. p./℃	HRMS(calcd.), m/z [M+H⁺]	IR, $ν ˙$ /cm^-1
3a^[11]	H	Ph		White solid		93	184—185		1585, 1510, 1444, 1230, 1037, 990, 812, 738, 698
3b	2-Me	Ph		Yellowish solid		62	96—97	588.1503 (588.1510)	1603, 1449, 1320, 1232, 1139, 1084, 1019, 970, 848, 802, 761, 729
3c	3-Me	Ph		Brown solid		73	79—80	588.1496 (588.1510)	1577, 1412, 1230, 1130, 1045, 887, 804, 761, 732
Compd.	R¹		R²		Appearance		Yield^a(%)	m. p./℃	HRMS(calcd.), m/z [M+H⁺]	IR, $ν ˙$ /cm^-1
3d	4-Me		Ph		Yellowish solid		84	171—172	588.1507 (588.1510)	1601, 1513, 1382, 1228, 1109, 1038, 857, 739, 696
3e	4-OMe		Ph		White solid		77	85—86	620.1425 (620.1408)	1725, 1593, 1510, 1297, 1258, 1105, 1026, 992, 804, 753, 701
3f	4-tBu		Ph		Yellowish solid		88	158—159	672.2430 (672.2449)	1659, 1513, 1386, 1235, 1089, 990, 830, 749, 701
3g	4-CF₃		Ph		Pale solid		87	208—209	696.0963 (696.0945)	1641, 1558, 1516, 1401, 1322, 1258, 1133, 1105, 962, 886, 829, 751
3h	4-F		Ph		White solid		82	201—202	596.1025 (596.1009)	1588, 1509, 1477, 1228, 1215, 1075, 1027, 989, 755, 659
3i	4-Cl		Ph		Pale solid		68	87—88	628.0406 (628.0418)	1609, 1581, 1509, 1461, 1233, 1075, 990, 882, 786, 724
3j	H		4-MeC₆H₄		Brown solid		92	191—192	588.1516 (588.1510)	1590, 1509, 1438, 1229, 1114, 1095, 1081, 1038, 875, 806, 772, 738, 722, 693
3k	H		4-OMeC₆H₄		Yellow solid		78	93—94	620.1416 (620.1408)	1603, 1512, 1467, 1289, 1243, 1173, 1106, 1036, 988, 822, 733
3l	H		3,4-(2Me)C₆H₄		Yellowish solid		65	74—75	616.1818 (616.1823)	1597, 1512, 1378, 1229, 1114, 1040, 989, 820, 732
3m	H		4-CF₃C₆H₄		Yellowish solid		86	81—82	696.0940 (696.0945)	1639, 1511, 1408, 1326, 1235, 1169, 1066, 992, 882, 752, 726
3n	H		4-FC₆H₄		White solid		87	177—178	596.1028 (596.1009)	1595, 1509, 1470, 1438, 1228, 1155, 1114, 1094, 1080, 1039, 993, 876, 828, 810, 755, 721
3o	H		4-ClC7H₄		Brown solid		90	86—87	628.0423 (628.0418)	1588, 1513, 1317, 1145, 1115, 1040, 1015, 991, 875, 812, 771, 747
3p	H		nC₄H₉		Yellow oil		51		492.1507 (492.1510)	1628, 1597, 1468, 1374, 1241, 1175, 1126, 917, 750
3q			Ph		Pale solid		57	75—76	572.0322 (572.0326)	1509, 1404, 1233, 1111, 990, 1044, 1021, 746, 726, 701
3r^b			Ph
3s	H		4-(NH₂)C₆H₄		Brown solid		45	95—96	590.1425 (590.1415)	3343,1608, 1509, 1466, 1210, 1178, 1044, 990, 747, 693, 665

Compd.	R¹	R²		Appearance		Yield^a(%)	m. p./℃	HRMS(calcd.), m/z [M+H⁺]	IR, $ν ˙$ /cm^-1
3a^[11]	H	Ph		White solid		93	184—185		1585, 1510, 1444, 1230, 1037, 990, 812, 738, 698
3b	2-Me	Ph		Yellowish solid		62	96—97	588.1503 (588.1510)	1603, 1449, 1320, 1232, 1139, 1084, 1019, 970, 848, 802, 761, 729
3c	3-Me	Ph		Brown solid		73	79—80	588.1496 (588.1510)	1577, 1412, 1230, 1130, 1045, 887, 804, 761, 732
Compd.	R¹		R²		Appearance		Yield^a(%)	m. p./℃	HRMS(calcd.), m/z [M+H⁺]	IR, $ν ˙$ /cm^-1
3d	4-Me		Ph		Yellowish solid		84	171—172	588.1507 (588.1510)	1601, 1513, 1382, 1228, 1109, 1038, 857, 739, 696
3e	4-OMe		Ph		White solid		77	85—86	620.1425 (620.1408)	1725, 1593, 1510, 1297, 1258, 1105, 1026, 992, 804, 753, 701
3f	4-tBu		Ph		Yellowish solid		88	158—159	672.2430 (672.2449)	1659, 1513, 1386, 1235, 1089, 990, 830, 749, 701
3g	4-CF₃		Ph		Pale solid		87	208—209	696.0963 (696.0945)	1641, 1558, 1516, 1401, 1322, 1258, 1133, 1105, 962, 886, 829, 751
3h	4-F		Ph		White solid		82	201—202	596.1025 (596.1009)	1588, 1509, 1477, 1228, 1215, 1075, 1027, 989, 755, 659
3i	4-Cl		Ph		Pale solid		68	87—88	628.0406 (628.0418)	1609, 1581, 1509, 1461, 1233, 1075, 990, 882, 786, 724
3j	H		4-MeC₆H₄		Brown solid		92	191—192	588.1516 (588.1510)	1590, 1509, 1438, 1229, 1114, 1095, 1081, 1038, 875, 806, 772, 738, 722, 693
3k	H		4-OMeC₆H₄		Yellow solid		78	93—94	620.1416 (620.1408)	1603, 1512, 1467, 1289, 1243, 1173, 1106, 1036, 988, 822, 733
3l	H		3,4-(2Me)C₆H₄		Yellowish solid		65	74—75	616.1818 (616.1823)	1597, 1512, 1378, 1229, 1114, 1040, 989, 820, 732
3m	H		4-CF₃C₆H₄		Yellowish solid		86	81—82	696.0940 (696.0945)	1639, 1511, 1408, 1326, 1235, 1169, 1066, 992, 882, 752, 726
3n	H		4-FC₆H₄		White solid		87	177—178	596.1028 (596.1009)	1595, 1509, 1470, 1438, 1228, 1155, 1114, 1094, 1080, 1039, 993, 876, 828, 810, 755, 721
3o	H		4-ClC7H₄		Brown solid		90	86—87	628.0423 (628.0418)	1588, 1513, 1317, 1145, 1115, 1040, 1015, 991, 875, 812, 771, 747
3p	H		nC₄H₉		Yellow oil		51		492.1507 (492.1510)	1628, 1597, 1468, 1374, 1241, 1175, 1126, 917, 750
3q			Ph		Pale solid		57	75—76	572.0322 (572.0326)	1509, 1404, 1233, 1111, 990, 1044, 1021, 746, 726, 701
3r^b			Ph
3s	H		4-(NH₂)C₆H₄		Brown solid		45	95—96	590.1425 (590.1415)	3343,1608, 1509, 1466, 1210, 1178, 1044, 990, 747, 693, 665

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(100 MHz, CDCl₃), δ						³¹P NMR(162 MHz, CDCl₃), δ
3a^[11]	7.80(dd,J=13.2, 8.0 Hz, 2H), 7.71(ddd, J=14.2, 7.6, 1.0 Hz, 1H), 7.59—7.48(m, 2H), 7.48—7.42(m, 2H), 7.41—7.36(m, 1H), 7.24—7.14(m, 6H), 7.07—7.00(m, 2H), 6.99—6.90(m, 3H)	139.45, 138.80(d,J=5 Hz), 137.23, 135.23(d, J=4 Hz), 132.84(d, J=2 Hz), 132.33(d, J=2 Hz), 132.18(d, J=1 Hz), 132.07(d, J=1 Hz), 131.64, 131.20, 130.20(d, J=11 Hz), 129.90, 129.29, 128.39, 128.25(d, J=1 Hz), 128.03, 127.55, 127.24, 127.10, 126.95, 126.85, 123.57, 122.32, 122.18(d, J=7 Hz)
Compd.	¹H NMR(400 MHz, CDCl₃), δ				¹³C NMR(100 MHz, CDCl₃), δ			³¹P NMR(162 MHz, CDCl₃), δ
3b	8.25(ddd,J=14.7, 7.6, 1.3 Hz, 1H), 7.53—7.46(m, 1H), 7.41(dd, J=7.5, 2.9 Hz, 1H), 7.39—7.33(m, 3H), 7.33—7.30(m, 1H), 7.26—7.22(m, 3H), 7.21—7.18(m, 2H), 7.16—7.03(m, 4H), 6.88(dd, J=8.1, 4.5 Hz, 1H), 2.29(s, 3H), 2.19(s, 3H)				146.27(d,J=11 Hz), 141.80(d, J=10 Hz), 140.55(d, J=11 Hz), 139.47(d, J=6 Hz), 136.66, 134.79(d, J=5 Hz), 134.45(d, J=12 Hz), 132.95(d, J=2 Hz), 132.19(d, J=2 Hz), 131.82, 131.48(d, J=12 Hz), 130.74, 130.22, 130.09, 129.33, 128.99, 128.79, 128.32, 127.70, 127.49, 125.87, 125.73, 125.15(d, J=9 Hz), 122.47, 121.21, 118.83(d, J=10 Hz), 21.32(d, J=6 Hz), 20.63(d, J=4 Hz)			21.69
3c	7.68(d,J=13.6 Hz, 1H), 7.62—7.45(m, 2H), 7.39—7.27(m, 3H), 7.25—7.12(m, 5H), 7.09(dd, J=8.3, 5.5 Hz, 1H), 7.02(dd, J=9.8, 6.1 Hz, 2H), 6.93(p, J=3.5 Hz, 3H), 2.37(d, J=6.7 Hz, 3H), 2.34(s, 3H)				138.55, 138.24, 138.10, 137.47, 137.33, 136.21(d,J=6 Hz), 135.36(d, J=4 Hz), 133.57(d, J=3 Hz), 133.29(d, J=2 Hz), 132.41(dd, J=11, 2 Hz ), 131.60, 131.32, 130.18,(d, J=11 Hz), 130.02, 129.36, 129.13(dd, J=11, 2 Hz ), 128.28, 128.14 , 128.10, 127.97, 127.50, 126.97, 126.85, 123.64, 122.40, 122.27(d, J=7 Hz), 21.29, 21.05			18.74
3d	7.67(dd,J=13.0, 7.9 Hz, 2H), 7.58(dd, J=14.0, 7.8 Hz, 1H), 7.26—7.21(m, 3H), 7.21—7.12(m, 5H), 7.06—7.00(m, 2H), 6.98(d, J=4.9 Hz, 1H), 6.96—6.89(m, 3H), 2.39(s, 3H), 2.31(s, 3H)				143.40(d,J=3 Hz), 142.70(d, J=2 Hz), 139.49, 138.76(d, J=6 Hz), 137.40, 135.45(d, J=3 Hz), 132.19(dd, J=11, 1 Hz ), 131.71, 130.26, 130.15, 129.32, 129.13, 128.99, 128.24, 128.11, 127.96, 127.48, 127.23, 127.14, 126.85, 122.10(d, J=2 Hz), 121.04, 119.76, 22.00, 21.69			18.83
3e	7.71(dd,J=12.2, 8.6 Hz, 2H), 7.62(dd, J=13.8, 8.5 Hz, 1H), 7.25—7.10(m, 5H), 7.03—6.99(m, 2H), 6.97—6.86(m, 6H), 6.66(dd, J=4.4, 2.4 Hz, 1H), 3.85(s, 3H), 3.70(s, 3H)				163.00(d,J=3 Hz), 162.56(d, J=3 Hz), 140.95(d, J=7 Hz), 140.13, 137.35, 135.47(d, J=4 Hz), 134.19(dd, J=13, 2 Hz), 132.21(d, J=12 Hz), 131.65, 131.56, 129.24, 128.15, 128.08, 128.01, 127.50, 126.91, 122.67, 121.54(d, J=6 Hz), 121.28, 113.81(d, J=14 Hz), 113.20(d, J=5 Hz), 112.98(d, J=10 Hz), 55.33, 55.15			18.75
3f	7.71(dd,J=12.8, 8.2 Hz, 2H), 7.65(dd, J=13.8, 8.1 Hz, 1H), 7.45(d, J=3.2 Hz, 1H), 7.44—7.37(m, 2H), 7.25—7.12(m, 6H), 7.04(d, J=2.9 Hz, 2H), 6.98—6.89(m, 3H), 1.31(s, 9H), 1.19(s, 9H)				156.35(d,J=3 Hz), 155.55(d, J=3 Hz), 139.32, 138.59(d, J=6 Hz), 137.53, 135.60(d, J=3 Hz), 132.04(dd, J=12, 2 Hz), 131.71, 130.05, 129.93, 129.40, 128.19, 128.08, 127.89, 127.50, 126.86, 126.82, 125.19(d, J=4 Hz), 124.58(d, J=4 Hz), 123.74(d, J=10 Hz), 122.09(d, J=7 Hz), 120.86, 119.58, 35.16, 35.08, 31.02, 30.92			18.48
3g	7.88(dd,J=12.9, 8.1 Hz, 2H), 7.77(dd, J=13.8, 8.0 Hz, 1H), 7.69(dd, J=8.2, 2.7 Hz, 2H), 7.57(d, J=7.9 Hz, 1H), 7.40(d, J=4.4 Hz, 1H), 7.24—7.02(m, 5H), 7.00—6.80(m, 5H)				141.31, 139.60(d,J=6 Hz), 135.91, 135.38, 134.92(dd, J=19, 3 Hz), 134.60(dd, J=18, 3 Hz), 134.45(d, J=3 Hz), 134.09, 132.33(dd, J=11, 2 Hz), 131.37, 131.10, 130.99, 129.02, 128.80, 128.48, 127.81, 127.63, 125.90, 125.56(q, J=4 Hz), 125.42(q, J=4 Hz), 124.65(d, J=3 Hz), 123.91—123.58(m), 121.93(d, J=3 Hz), 121.53(d, J=7 Hz)			15.38
3h	7.86—7.75(m, 2H), 7.74—7.67(m, 1H), 7.29—7.11(m, 7H), 7.11—7.06(m, 1H), 7.04—6.98(m, 2H), 6.98—6.91(m, 3H), 6.89—6.85(m, 1H)				166.72(dd,J=24, 4 Hz), 164.20(dd, J=18, 4 Hz), 141.96(dd, J=9, 7 Hz), 140.98, 136.58, 134.85, 134.73, 134.63, 132.99(dd, J=13, 10 Hz), 131.47, 129.06, 128.54, 128.30, 127.69, 127.32, 121.03(dd, J=7, 3 Hz), 119.29(d, J=3 Hz), 118.99(d, J=2 Hz), 115.93(dd, J=21, 15 Hz), 115.04(dd, J=22, 5 Hz), 113.62(dd, J=23, 11 Hz)			16.77
Compd.	¹H NMR(400 MHz, CDCl₃), δ		¹³C NMR(100 MHz, CDCl₃), δ			³¹P NMR(162 MHz, CDCl₃), δ
3i	7.72(dd,J=12.8, 8.2 Hz, 2H), 7.63(dd, J=13.9, 8.2 Hz, 1H), 7.46(dd, J=8.4, 2.8 Hz, 2H), 7.37(dt, J=8.2, 2.1 Hz, 1H), 7.26—7.21(m, 2H), 7.21—7.15(m, 2H), 7.15—7.09(m, 2H), 7.05—6.90(m, 5H)		141.04, 140.57(d,J=7 Hz), 139.80(d, J=5 Hz), 139.38(d, J=3 Hz), 136.33, 134.73(d, J=3 Hz), 133.37(dd, J=12, 2 Hz), 131.68(d, J=12 Hz), 131.47, 129.69, 129.06, 129.00, 128.85, 128.59, 128.33, 127.70, 127.67, 127.53, 127.38, 126.79(d, J=10 Hz), 121.32, 121.16, 121.09, 120.04			16.78
3j	7.79(dd,J=13.2, 7.9 Hz, 2H), 7.727.67(m, 1H), 7.57—7.40(m, 4H), 7.39—7.33(m, 1H), 7.20(dd, J=8.0, 5.2 Hz, 1H), 7.08—7.00(m, 4H), 6.92(d, J=7.9 Hz, 2H), 6.74(d, J=7.9 Hz, 2H), 2.27(s, 3H), 2.09(s, 3H)		139.36, 139.19(d,J=6 Hz), 137.91, 136.40, 134.29, 132.76(d, J=3 Hz), 132.42(d, J=4 Hz), 132.23(d, J=3 Hz), 132.06(q, J=1 Hz), 131.42, 131.35, 130.01(d, J=11 Hz), 129.17, 128.74, 128.35, 128.27, 128.22, 127.08, 126.96(d, J=4 Hz), 126.88, 123.61, 122.31(d, J=8 Hz), 21.15, 21.13			18.25
3k	7.78(dd,J=13.2, 7.7 Hz, 2H), 7.73—7.64(m, 1H), 7.58—7.47(m, 2H), 7.43(td, J=7.5, 3.5 Hz, 2H), 7.36(td, J=7.4, 2.8 Hz, 1H), 7.23(dd, J=8.0, 5.2 Hz, 1H), 7.07(d, J=8.6 Hz, 2H), 6.95(d, J=8.6 Hz, 2H), 6.77(d, J=8.7 Hz, 2H), 6.47(d, J=8.8 Hz, 2H), 3.76(s, 3H), 3.62(s, 3H)		158.92, 158.25, 139.33(t,J=5 Hz), 132.77(d, J=2 Hz), 132.62, 132.12(td, J=12, 3 Hz), 130.65, 130.08, 129.96, 129.63, 128.28(d, J=13 Hz), 127.82(d, J=3 Hz), 127.05, 126.91, 126.81, 123.58, 122.32, 121.94(d, J=2 Hz), 116.20, 114.88, 113.49, 112.96, 55.09, 54.90			18.28
3l	7.79(dd,J=13.1, 7.6 Hz, 2H), 7.67(dd, J=14.3, 7.1 Hz, 1H), 7.567.39(m, 4H), 7.35(td, J=7.4, 2.6 Hz, 1H), 7.21(dd, J=7.9, 5.2 Hz, 1H), 6.96(d, J=8.0 Hz, 2H), 6.916.80(m, 2H), 6.76(d, J=7.7 Hz, 1H), 6.67(d, J=7.8 Hz, 1H), 2.18(s, 3H), 2.17(s, 3H), 2.00(s, 3H), 1.96(s, 3H)		139.40(d,J=5 Hz), 139.21, 136.46, 135.88, 135.51, 134.92, 134.72, 132.79, 132.73(d, J=3 Hz), 132.15(d, J=2 Hz), 132.05, 131.31, 130.43, 130.01, 129.86(d, J=3 Hz), 129.17, 128.95, 128.68, 128.25(d, J=4 Hz), 127.04(t, J=8 Hz), 126.82, 123.67, 122.48(t, J=7 Hz), 19.66, 19.43, 19.26			19.19
3m	7.79(dd,J=13.2, 7.7 Hz, 2H), 7.75—7.68(m, 1H), 7.58(dd, J=12.1, 4.5 Hz, 2H), 7.52(d, J=8.2 Hz, 2H), 7.49—7.43(m, 3H), 7.31(d, J=8.0 Hz, 2H), 7.29—7.25(m, 2H), 7.18(d, J=8.1 Hz, 2H), 7.12(dd, J=8.0, 5.2 Hz, 1H)		140.62, 138.43, 138.11, 137.60(d,J=6 Hz), 133.28(d, J=3 Hz), 133.05, 132.63(d, J=2 Hz), 132.28(d, J=10 Hz), 131.95, 130.77, 130.46(d, J=12 Hz), 129.68, 129.52, 128.68, 128.50(d, J=13 Hz), 128.44(d, J=14 Hz), 126.74(d, J=9 Hz), 125.29(q, J=4 Hz), 124.90(q, J=4 Hz), 124.68, 123.96, 122.70, 122.48, 122.14(d, J=7 Hz), 121.98			17.78
3n	7.77(dd,J=13.1, 7.6 Hz, 2H), 7.69(dd, J=14.2, 7.4 Hz, 1H), 7.54(dd, J=16.2, 8.1 Hz, 2H), 7.48—7.36(m, 3H), 7.21—7.07(m, 3H), 7.02(dd, J=7.8, 5.6 Hz, 2H), 6.94(t, J=8.6 Hz, 2H), 6.68(t, J=8.6 Hz, 2H)		163.30, 162.95, 160.82, 160.50, 138.75, 138.44(d,J=5 Hz), 133.16(d, J=8 Hz), 133.03(d, J=3 Hz), 132.44(d, J=2 Hz), 132.20(dd, J=11, 1 Hz), 131.27, 131.15(d, J=8 Hz), 130.61, 130.33(d, J=12 Hz), 129.30, 128.39(d, J=14 Hz), 127.43(d, J=4 Hz), 126.75(d, J=10 Hz), 123.71, 122.45, 121.52(d, J=7 Hz), 115.13(dd, J=28, 22 Hz)			17.86
3o	7.76(dd,J=13.2, 7.8 Hz, 2H), 7.72—7.66(m, 1H), 7.59—7.49(m, 2H), 7.48—7.39(m, 3H), 7.24(d, J=8.4 Hz, 2H), 7.15(dd, J=8.0, 5.2 Hz, 1H), 7.13—7.06(m, 2H), 6.98(s, 4H)		138.42, 138.14(d,J=5 Hz), 135.44, 134.56, 133.55(d, J=4 Hz), 133.31, 133.10(d, J=3 Hz), 132.86, 132.49(d, J=2 Hz), 132.22(dd, J=10, 2 Hz), 130.56, 130.40, 130.29, 129.12, 128.58, 128.49, 128.36, 128.22, 127.66, 127.52, 126.75(d, J=9 Hz), 123.82, 122.56, 121.64(d, J=6 Hz)			17.82
Compd.	¹H NMR(400 MHz, CDCl₃), δ			¹³C NMR(100 MHz, CDCl₃), δ			³¹P NMR(162 MHz, CDCl₃), δ
3p	7.86—7.71(m, 2H), 7.62—7.52(m, 2H), 7.52—7.38(m, 4H), 7.32—7.23(m, 1H), 2.67—2.38(m, 4H), 1.76—1.51(m, 4H), 1.03(t, J=7.4 Hz, 3H), 0.94(t, J=7.4 Hz, 3H)			149.69(d,J=11 Hz), 137.49(d, J=6 Hz), 132.53(dd, J=14, 2 Hz), 132.07, 131.96, 130.91, 130.40(d, J=13 Hz), 129.48, 128.33, 128.19, 126.56(d, J=15 Hz), 124.09, 123.63(d, J=10 Hz), 122.80, 113.76, 113.64, 33.99(d, J=5 Hz), 29.67, 22.58, 20.16, 14.09, 13.59			23.93
3q	7.77—7.75(m, 1H), 7.66(dd, J=5.9, 5.0 Hz, 1H), 7.59(dd, J=8.3, 3.6 Hz, 1H), 7.24—7.09(m, 6H), 7.04(d, J=7.6 Hz, 2H), 7.00—6.92(m, 3H), 6.85(dd, J=4.9, 2.7 Hz, 1H)			148.21(d,J=7 Hz), 140.12, 137.70, 137.29(dd, J=13, 2 Hz), 135.47,(d, J=6 Hz), 134.50(d, J=4 Hz), 133.26(d, J=9 Hz), 132.95, 131.37, 130.88, 129.39, 128.45, 128.28, 128.06, 127.67, 127.33, 127.20, 126.97, 119.69, 118.19(d, J=5 Hz)			6.87
3r^*
3s	7.77(dd,J=13.2, 7.8 Hz, 2H), 7.68(ddd, J=14.1, 7.6, 1.1 Hz, 1H), 7.56—7.46(m, 2H), 7.45—7.39(m, 2H), 7.37—7.27(m, 2H), 6.97—6.89(m, 2H), 6.81(d, J=8.4 Hz, 2H), 6.60—6.51(m, 2H), 6.28—6.20(m, 2H), 3.60(s, 2H), 3.52(s, 2H)			145.90, 144.89, 139.76(d,J=2 Hz), 139.69, 132.70(d, J=3 Hz), 132.49, 132.18(d, J=3 Hz), 132.03(dd, J=11, 1 Hz), 131.51, 130.54, 130.22, 129.89(d, J=12 Hz), 128.35, 128.21, 127.72, 126.97, 126.85(d, J=5 Hz), 126.68, 125.80(d, J=4 Hz), 123.53, 122.27, 121.99(d, J=6 Hz), 114.81, 114.03			18.56

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(100 MHz, CDCl₃), δ						³¹P NMR(162 MHz, CDCl₃), δ
3a^[11]	7.80(dd,J=13.2, 8.0 Hz, 2H), 7.71(ddd, J=14.2, 7.6, 1.0 Hz, 1H), 7.59—7.48(m, 2H), 7.48—7.42(m, 2H), 7.41—7.36(m, 1H), 7.24—7.14(m, 6H), 7.07—7.00(m, 2H), 6.99—6.90(m, 3H)	139.45, 138.80(d,J=5 Hz), 137.23, 135.23(d, J=4 Hz), 132.84(d, J=2 Hz), 132.33(d, J=2 Hz), 132.18(d, J=1 Hz), 132.07(d, J=1 Hz), 131.64, 131.20, 130.20(d, J=11 Hz), 129.90, 129.29, 128.39, 128.25(d, J=1 Hz), 128.03, 127.55, 127.24, 127.10, 126.95, 126.85, 123.57, 122.32, 122.18(d, J=7 Hz)
Compd.	¹H NMR(400 MHz, CDCl₃), δ				¹³C NMR(100 MHz, CDCl₃), δ			³¹P NMR(162 MHz, CDCl₃), δ
3b	8.25(ddd,J=14.7, 7.6, 1.3 Hz, 1H), 7.53—7.46(m, 1H), 7.41(dd, J=7.5, 2.9 Hz, 1H), 7.39—7.33(m, 3H), 7.33—7.30(m, 1H), 7.26—7.22(m, 3H), 7.21—7.18(m, 2H), 7.16—7.03(m, 4H), 6.88(dd, J=8.1, 4.5 Hz, 1H), 2.29(s, 3H), 2.19(s, 3H)				146.27(d,J=11 Hz), 141.80(d, J=10 Hz), 140.55(d, J=11 Hz), 139.47(d, J=6 Hz), 136.66, 134.79(d, J=5 Hz), 134.45(d, J=12 Hz), 132.95(d, J=2 Hz), 132.19(d, J=2 Hz), 131.82, 131.48(d, J=12 Hz), 130.74, 130.22, 130.09, 129.33, 128.99, 128.79, 128.32, 127.70, 127.49, 125.87, 125.73, 125.15(d, J=9 Hz), 122.47, 121.21, 118.83(d, J=10 Hz), 21.32(d, J=6 Hz), 20.63(d, J=4 Hz)			21.69
3c	7.68(d,J=13.6 Hz, 1H), 7.62—7.45(m, 2H), 7.39—7.27(m, 3H), 7.25—7.12(m, 5H), 7.09(dd, J=8.3, 5.5 Hz, 1H), 7.02(dd, J=9.8, 6.1 Hz, 2H), 6.93(p, J=3.5 Hz, 3H), 2.37(d, J=6.7 Hz, 3H), 2.34(s, 3H)				138.55, 138.24, 138.10, 137.47, 137.33, 136.21(d,J=6 Hz), 135.36(d, J=4 Hz), 133.57(d, J=3 Hz), 133.29(d, J=2 Hz), 132.41(dd, J=11, 2 Hz ), 131.60, 131.32, 130.18,(d, J=11 Hz), 130.02, 129.36, 129.13(dd, J=11, 2 Hz ), 128.28, 128.14 , 128.10, 127.97, 127.50, 126.97, 126.85, 123.64, 122.40, 122.27(d, J=7 Hz), 21.29, 21.05			18.74
3d	7.67(dd,J=13.0, 7.9 Hz, 2H), 7.58(dd, J=14.0, 7.8 Hz, 1H), 7.26—7.21(m, 3H), 7.21—7.12(m, 5H), 7.06—7.00(m, 2H), 6.98(d, J=4.9 Hz, 1H), 6.96—6.89(m, 3H), 2.39(s, 3H), 2.31(s, 3H)				143.40(d,J=3 Hz), 142.70(d, J=2 Hz), 139.49, 138.76(d, J=6 Hz), 137.40, 135.45(d, J=3 Hz), 132.19(dd, J=11, 1 Hz ), 131.71, 130.26, 130.15, 129.32, 129.13, 128.99, 128.24, 128.11, 127.96, 127.48, 127.23, 127.14, 126.85, 122.10(d, J=2 Hz), 121.04, 119.76, 22.00, 21.69			18.83
3e	7.71(dd,J=12.2, 8.6 Hz, 2H), 7.62(dd, J=13.8, 8.5 Hz, 1H), 7.25—7.10(m, 5H), 7.03—6.99(m, 2H), 6.97—6.86(m, 6H), 6.66(dd, J=4.4, 2.4 Hz, 1H), 3.85(s, 3H), 3.70(s, 3H)				163.00(d,J=3 Hz), 162.56(d, J=3 Hz), 140.95(d, J=7 Hz), 140.13, 137.35, 135.47(d, J=4 Hz), 134.19(dd, J=13, 2 Hz), 132.21(d, J=12 Hz), 131.65, 131.56, 129.24, 128.15, 128.08, 128.01, 127.50, 126.91, 122.67, 121.54(d, J=6 Hz), 121.28, 113.81(d, J=14 Hz), 113.20(d, J=5 Hz), 112.98(d, J=10 Hz), 55.33, 55.15			18.75
3f	7.71(dd,J=12.8, 8.2 Hz, 2H), 7.65(dd, J=13.8, 8.1 Hz, 1H), 7.45(d, J=3.2 Hz, 1H), 7.44—7.37(m, 2H), 7.25—7.12(m, 6H), 7.04(d, J=2.9 Hz, 2H), 6.98—6.89(m, 3H), 1.31(s, 9H), 1.19(s, 9H)				156.35(d,J=3 Hz), 155.55(d, J=3 Hz), 139.32, 138.59(d, J=6 Hz), 137.53, 135.60(d, J=3 Hz), 132.04(dd, J=12, 2 Hz), 131.71, 130.05, 129.93, 129.40, 128.19, 128.08, 127.89, 127.50, 126.86, 126.82, 125.19(d, J=4 Hz), 124.58(d, J=4 Hz), 123.74(d, J=10 Hz), 122.09(d, J=7 Hz), 120.86, 119.58, 35.16, 35.08, 31.02, 30.92			18.48
3g	7.88(dd,J=12.9, 8.1 Hz, 2H), 7.77(dd, J=13.8, 8.0 Hz, 1H), 7.69(dd, J=8.2, 2.7 Hz, 2H), 7.57(d, J=7.9 Hz, 1H), 7.40(d, J=4.4 Hz, 1H), 7.24—7.02(m, 5H), 7.00—6.80(m, 5H)				141.31, 139.60(d,J=6 Hz), 135.91, 135.38, 134.92(dd, J=19, 3 Hz), 134.60(dd, J=18, 3 Hz), 134.45(d, J=3 Hz), 134.09, 132.33(dd, J=11, 2 Hz), 131.37, 131.10, 130.99, 129.02, 128.80, 128.48, 127.81, 127.63, 125.90, 125.56(q, J=4 Hz), 125.42(q, J=4 Hz), 124.65(d, J=3 Hz), 123.91—123.58(m), 121.93(d, J=3 Hz), 121.53(d, J=7 Hz)			15.38
3h	7.86—7.75(m, 2H), 7.74—7.67(m, 1H), 7.29—7.11(m, 7H), 7.11—7.06(m, 1H), 7.04—6.98(m, 2H), 6.98—6.91(m, 3H), 6.89—6.85(m, 1H)				166.72(dd,J=24, 4 Hz), 164.20(dd, J=18, 4 Hz), 141.96(dd, J=9, 7 Hz), 140.98, 136.58, 134.85, 134.73, 134.63, 132.99(dd, J=13, 10 Hz), 131.47, 129.06, 128.54, 128.30, 127.69, 127.32, 121.03(dd, J=7, 3 Hz), 119.29(d, J=3 Hz), 118.99(d, J=2 Hz), 115.93(dd, J=21, 15 Hz), 115.04(dd, J=22, 5 Hz), 113.62(dd, J=23, 11 Hz)			16.77
Compd.	¹H NMR(400 MHz, CDCl₃), δ		¹³C NMR(100 MHz, CDCl₃), δ			³¹P NMR(162 MHz, CDCl₃), δ
3i	7.72(dd,J=12.8, 8.2 Hz, 2H), 7.63(dd, J=13.9, 8.2 Hz, 1H), 7.46(dd, J=8.4, 2.8 Hz, 2H), 7.37(dt, J=8.2, 2.1 Hz, 1H), 7.26—7.21(m, 2H), 7.21—7.15(m, 2H), 7.15—7.09(m, 2H), 7.05—6.90(m, 5H)		141.04, 140.57(d,J=7 Hz), 139.80(d, J=5 Hz), 139.38(d, J=3 Hz), 136.33, 134.73(d, J=3 Hz), 133.37(dd, J=12, 2 Hz), 131.68(d, J=12 Hz), 131.47, 129.69, 129.06, 129.00, 128.85, 128.59, 128.33, 127.70, 127.67, 127.53, 127.38, 126.79(d, J=10 Hz), 121.32, 121.16, 121.09, 120.04			16.78
3j	7.79(dd,J=13.2, 7.9 Hz, 2H), 7.727.67(m, 1H), 7.57—7.40(m, 4H), 7.39—7.33(m, 1H), 7.20(dd, J=8.0, 5.2 Hz, 1H), 7.08—7.00(m, 4H), 6.92(d, J=7.9 Hz, 2H), 6.74(d, J=7.9 Hz, 2H), 2.27(s, 3H), 2.09(s, 3H)		139.36, 139.19(d,J=6 Hz), 137.91, 136.40, 134.29, 132.76(d, J=3 Hz), 132.42(d, J=4 Hz), 132.23(d, J=3 Hz), 132.06(q, J=1 Hz), 131.42, 131.35, 130.01(d, J=11 Hz), 129.17, 128.74, 128.35, 128.27, 128.22, 127.08, 126.96(d, J=4 Hz), 126.88, 123.61, 122.31(d, J=8 Hz), 21.15, 21.13			18.25
3k	7.78(dd,J=13.2, 7.7 Hz, 2H), 7.73—7.64(m, 1H), 7.58—7.47(m, 2H), 7.43(td, J=7.5, 3.5 Hz, 2H), 7.36(td, J=7.4, 2.8 Hz, 1H), 7.23(dd, J=8.0, 5.2 Hz, 1H), 7.07(d, J=8.6 Hz, 2H), 6.95(d, J=8.6 Hz, 2H), 6.77(d, J=8.7 Hz, 2H), 6.47(d, J=8.8 Hz, 2H), 3.76(s, 3H), 3.62(s, 3H)		158.92, 158.25, 139.33(t,J=5 Hz), 132.77(d, J=2 Hz), 132.62, 132.12(td, J=12, 3 Hz), 130.65, 130.08, 129.96, 129.63, 128.28(d, J=13 Hz), 127.82(d, J=3 Hz), 127.05, 126.91, 126.81, 123.58, 122.32, 121.94(d, J=2 Hz), 116.20, 114.88, 113.49, 112.96, 55.09, 54.90			18.28
3l	7.79(dd,J=13.1, 7.6 Hz, 2H), 7.67(dd, J=14.3, 7.1 Hz, 1H), 7.567.39(m, 4H), 7.35(td, J=7.4, 2.6 Hz, 1H), 7.21(dd, J=7.9, 5.2 Hz, 1H), 6.96(d, J=8.0 Hz, 2H), 6.916.80(m, 2H), 6.76(d, J=7.7 Hz, 1H), 6.67(d, J=7.8 Hz, 1H), 2.18(s, 3H), 2.17(s, 3H), 2.00(s, 3H), 1.96(s, 3H)		139.40(d,J=5 Hz), 139.21, 136.46, 135.88, 135.51, 134.92, 134.72, 132.79, 132.73(d, J=3 Hz), 132.15(d, J=2 Hz), 132.05, 131.31, 130.43, 130.01, 129.86(d, J=3 Hz), 129.17, 128.95, 128.68, 128.25(d, J=4 Hz), 127.04(t, J=8 Hz), 126.82, 123.67, 122.48(t, J=7 Hz), 19.66, 19.43, 19.26			19.19
3m	7.79(dd,J=13.2, 7.7 Hz, 2H), 7.75—7.68(m, 1H), 7.58(dd, J=12.1, 4.5 Hz, 2H), 7.52(d, J=8.2 Hz, 2H), 7.49—7.43(m, 3H), 7.31(d, J=8.0 Hz, 2H), 7.29—7.25(m, 2H), 7.18(d, J=8.1 Hz, 2H), 7.12(dd, J=8.0, 5.2 Hz, 1H)		140.62, 138.43, 138.11, 137.60(d,J=6 Hz), 133.28(d, J=3 Hz), 133.05, 132.63(d, J=2 Hz), 132.28(d, J=10 Hz), 131.95, 130.77, 130.46(d, J=12 Hz), 129.68, 129.52, 128.68, 128.50(d, J=13 Hz), 128.44(d, J=14 Hz), 126.74(d, J=9 Hz), 125.29(q, J=4 Hz), 124.90(q, J=4 Hz), 124.68, 123.96, 122.70, 122.48, 122.14(d, J=7 Hz), 121.98			17.78
3n	7.77(dd,J=13.1, 7.6 Hz, 2H), 7.69(dd, J=14.2, 7.4 Hz, 1H), 7.54(dd, J=16.2, 8.1 Hz, 2H), 7.48—7.36(m, 3H), 7.21—7.07(m, 3H), 7.02(dd, J=7.8, 5.6 Hz, 2H), 6.94(t, J=8.6 Hz, 2H), 6.68(t, J=8.6 Hz, 2H)		163.30, 162.95, 160.82, 160.50, 138.75, 138.44(d,J=5 Hz), 133.16(d, J=8 Hz), 133.03(d, J=3 Hz), 132.44(d, J=2 Hz), 132.20(dd, J=11, 1 Hz), 131.27, 131.15(d, J=8 Hz), 130.61, 130.33(d, J=12 Hz), 129.30, 128.39(d, J=14 Hz), 127.43(d, J=4 Hz), 126.75(d, J=10 Hz), 123.71, 122.45, 121.52(d, J=7 Hz), 115.13(dd, J=28, 22 Hz)			17.86
3o	7.76(dd,J=13.2, 7.8 Hz, 2H), 7.72—7.66(m, 1H), 7.59—7.49(m, 2H), 7.48—7.39(m, 3H), 7.24(d, J=8.4 Hz, 2H), 7.15(dd, J=8.0, 5.2 Hz, 1H), 7.13—7.06(m, 2H), 6.98(s, 4H)		138.42, 138.14(d,J=5 Hz), 135.44, 134.56, 133.55(d, J=4 Hz), 133.31, 133.10(d, J=3 Hz), 132.86, 132.49(d, J=2 Hz), 132.22(dd, J=10, 2 Hz), 130.56, 130.40, 130.29, 129.12, 128.58, 128.49, 128.36, 128.22, 127.66, 127.52, 126.75(d, J=9 Hz), 123.82, 122.56, 121.64(d, J=6 Hz)			17.82
Compd.	¹H NMR(400 MHz, CDCl₃), δ			¹³C NMR(100 MHz, CDCl₃), δ			³¹P NMR(162 MHz, CDCl₃), δ
3p	7.86—7.71(m, 2H), 7.62—7.52(m, 2H), 7.52—7.38(m, 4H), 7.32—7.23(m, 1H), 2.67—2.38(m, 4H), 1.76—1.51(m, 4H), 1.03(t, J=7.4 Hz, 3H), 0.94(t, J=7.4 Hz, 3H)			149.69(d,J=11 Hz), 137.49(d, J=6 Hz), 132.53(dd, J=14, 2 Hz), 132.07, 131.96, 130.91, 130.40(d, J=13 Hz), 129.48, 128.33, 128.19, 126.56(d, J=15 Hz), 124.09, 123.63(d, J=10 Hz), 122.80, 113.76, 113.64, 33.99(d, J=5 Hz), 29.67, 22.58, 20.16, 14.09, 13.59			23.93
3q	7.77—7.75(m, 1H), 7.66(dd, J=5.9, 5.0 Hz, 1H), 7.59(dd, J=8.3, 3.6 Hz, 1H), 7.24—7.09(m, 6H), 7.04(d, J=7.6 Hz, 2H), 7.00—6.92(m, 3H), 6.85(dd, J=4.9, 2.7 Hz, 1H)			148.21(d,J=7 Hz), 140.12, 137.70, 137.29(dd, J=13, 2 Hz), 135.47,(d, J=6 Hz), 134.50(d, J=4 Hz), 133.26(d, J=9 Hz), 132.95, 131.37, 130.88, 129.39, 128.45, 128.28, 128.06, 127.67, 127.33, 127.20, 126.97, 119.69, 118.19(d, J=5 Hz)			6.87
3r^*
3s	7.77(dd,J=13.2, 7.8 Hz, 2H), 7.68(ddd, J=14.1, 7.6, 1.1 Hz, 1H), 7.56—7.46(m, 2H), 7.45—7.39(m, 2H), 7.37—7.27(m, 2H), 6.97—6.89(m, 2H), 6.81(d, J=8.4 Hz, 2H), 6.60—6.51(m, 2H), 6.28—6.20(m, 2H), 3.60(s, 2H), 3.52(s, 2H)			145.90, 144.89, 139.76(d,J=2 Hz), 139.69, 132.70(d, J=3 Hz), 132.49, 132.18(d, J=3 Hz), 132.03(dd, J=11, 1 Hz), 131.51, 130.54, 130.22, 129.89(d, J=12 Hz), 128.35, 128.21, 127.72, 126.97, 126.85(d, J=5 Hz), 126.68, 125.80(d, J=4 Hz), 123.53, 122.27, 121.99(d, J=6 Hz), 114.81, 114.03			18.56

Entry	Base	Oxidant	Solvent	Yield^b(%)	Entry	Base	Oxidant	Solvent	Yield^b(%)
1	K₃PO₄	Ag₂CO₃	^tBuOH	37	11	NaHCO₃	AgOAc	^tBuOH	27
2	Na₃PO₄	Ag₂CO₃	^tBuOH	32	12	NaHCO₃	AgOOCCF₃	^tBuOH	14
3	Na₂HPO₄	Ag₂CO₃	^tBuOH	67	13	NaHCO₃	AgF	^tBuOH	20
4	NaH₂PO₄	Ag₂CO₃	^tBuOH	81	14	NaHCO₃	Ag₂CO₃	EtOH	39
5	K₂CO₃	Ag₂CO₃	^tBuOH	18	15	NaHCO₃	Ag₂CO₃	PhMe	78
6	Na₂CO₃	Ag₂CO₃	^tBuOH	78	16	NaHCO₃	Ag₂CO₃	Xylene	80
7	NaHCO₃	Ag₂CO₃	^tBuOH	88	17	NaHCO₃	Ag₂CO₃	DCE	93
8	KOAc	Ag₂CO₃	^tBuOH	28	18	NaHCO₃	Ag₂CO₃	THF	65
9	NaOAc	Ag₂CO₃	^tBuOH	45	19	NaHCO₃	Ag₂CO₃	1,4-Dioxane	84
10	NaHCO₃	Ag₂O	^tBuOH	53	20	NaHCO₃	Ag₂CO₃	CH₃CN	45

Scheme 3 Proposed mechanism of C—H activation/cyclization

References 25

[1]	Tang X., Du Z., Wu G., Han F., Chem. Res. Chinese Universities, 2019, 35( 5), 812— 816
[2]	Feng X., He J., Wang X., Wang G., Wang X., Peng H., Chem. Res. Chinese Universities, 2018, 34( 3), 444— 450
[3]	Keglevich G ., Organophosphorus Chemistry: Novel Developments, Walter de Gruyter, Berlin, 2018, 232— 247
[4]	He J., Wasa M., Chan K. S. L., Shao Q., Yu J. Q., Chem. Rev., 2017, 117( 13), 8754— 8786
[5]	Gensch T., Hopkinson M. N., Glorius F., Wencel-Delord J., Chem. Soc. Rev., 2016, 45( 10), 2900— 2936
[6]	Zhou C. N., Zheng Z. A., Chang G., Xiao Y. C., Shen Y. H., Li G., Zhang Y. M., Peng W. M., Wang L., Xiao B., Current Organic Chemistry, 2019, 23( 2), 103— 135
[7]	Chen Z., Wang B., Zhang J., Yu W., Liu Z., Zhang Y., Org. Chem. Front., 2015, 2( 9), 11071295
[8]	Yao X., Jin L., Rao Y., Asian J. Org. Chem., 2017, 6( 7), 825— 830
[9]	Ma Y. N., Li S. X., Yang S. D., Acc. Chem. Res., 2017, 50( 6), 1480— 1492
[10]	Zhao D., Nimphius C., Lindale M., Glorius F., Org. Lett., 2013, 15( 17), 4504— 4507
[11]	Park S., Seo B., Shin S., Son J. Y., Lee P. H., Chem. Commun., 2013, 49( 77), 8671— 8673
[12]	Lin Z. Q., Wang W. Z., Yan S. B., Duan W. L., Angew. Chem. Int. Ed., 2015, 54( 21), 6265— 6269
[13]	Li S. S., Wu L., Qin L., Zhu Y. Q., Su F., Xu Y. J., Dong L., Org. Lett., 2016, 18( 17), 4214— 4217
[14]	Guan J., Wu G. J., Han F. S., Chem. Eur. J., 2014, 20( 12), 3301— 3305
[15]	Sun Y., Cramer N., Angew. Chem. Int. Ed., 2017, 56( 1), 364— 367
[16]	Li J., Liu H., Meng F., Yan L., Shi Y., Zhang Y., Gu Q., Chem. Res. Chinese Universities, 2018, 34( 2), 197— 202
[17]	Wang L., Li Z., Qu X., Peng W. M., Tetrahedron Lett., 2015, 56( 24), 3754— 3757
[18]	Wang L., Li Z., Qu X., Peng W. M., Hu S. Q., Tetrahedron Lett., 2015, 56( 45), 6214— 6218
[19]	Wang L., Qu X., Fang L., Hu S., Wang F., Eur. J. Org. Chem., 2016, 33( 33), 5494— 5501
[20]	Zhou C. N., Xie H. H., Zheng Z. A., Xiao Y. C., Li G., Shen Y. H., Peng W. M., Wang L., Chem. Eur. J., 2018, 24( 21), 5469— 5473
[21]	Purser S., Moore P. R., Swallow S., Gouverneur V., Chem. Soc. Rev., 2008, 37( 2), 320— 330
[22]	Armarego W L. F., Chai C. L. L., Purification of Laboratory Chemicals, Translated by Lin Y. J., Liu W., Wang H. P., Sun X. B., Li Q. S., Cao J. G., Chemical Industry Press,Beijing, 2007, 65— 365
	( 林英杰, 刘伟, 王会萍, 孙晓波, 李青山 , 曹军刚[译]. 实验室化学品纯化手册, 北京: 化学工业出版社, 2007, 65— 365)
[23]	Unoh Y., Hashimoto Y., Takeda D., Hirano K., Satoh T., Miura M., Org. Lett., 2013, 15( 13), 3528— 3561
[24]	Seo J., Park Y., Jeon I., Ryu T., Park S., Lee P. H., Org. Lett., 2013, 15( 13), 3358— 3361
[25]	Park Y., Seo J., Park S., Yoo E. J., Lee P. H., Chem. Eur. J., 2013, 19( 48), 16461— 16468