微波辅助下铑催化二芳基膦酰胺与炔烃的C—H活化/环化反应

doi:10.7503/cjcu20190571

摘要/Abstract

摘要：

研究了微波条件下[RhCp ^*Cl₂]₂(Cp ^*: 五甲基环戊二烯基)催化二芳基膦酰胺与炔烃的C—H活化/环化反应, 以中等到较好的收率获得了一系列具有环状结构的含氟膦酰胺衍生物. 通过考察溶剂、温度、时间以及碱等因素, 筛选了最佳反应条件. 对该催化体系进行放大量实验, 也获得了良好的结果. 在实验基础上, 推测了可能的反应机理, 并将此方法应用于一种新型含氟代环状膦酰胺二胺单体的制备.

关键词: 微波, [RhCp ^*Cl₂]₂, C—H活化/环化反应;, 二芳基膦酰胺

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

中图分类号:

O626.1

TrendMD:

周春妮, 郑子昂, 彭望明, 王洪波, 张玉敏, 王亮, 肖标. 微波辅助下铑催化二芳基膦酰胺与炔烃的C—H活化/环化反应. 高等学校化学学报, 2020, 41(4): 726.

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 ^†. Chem. J. Chinese Universities, 2020, 41(4): 726.

图/表 5

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

Table 1 Appearance, yields, melting points, HRMS and IR data of compounds 3a—3s

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

Table 1 Appearance, yields, melting points, HRMS and IR data of compounds 3a—3s

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

Table 2 1H NMR, 13C NMR and 31P NMR data of compounds 3a—3s

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

Table 2 1H NMR, 13C NMR and 31P NMR data of compounds 3a—3s

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

Table 3 Optimization of the reaction conditionsa

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

参考文献 25

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