S. Coufourier, D. Ndiaye, Q.G. Gaillard et al.
Tetrahedron xxx (xxxx) xxx
32.2 ppm. HRMS: MHþ, found: 223.1123. C16H15
223.1123.
O
requires
207.2, 153.3, 143.8, 136.4, 135, 129.3, 127.6, 126.6, 126.5 (1C, q, JC-
¼ 3.7 Hz), 123.2, 48.6, 36.7, 32.1 ppm. 19F NMR (500 MHz, CDCl3)
d:
F
62.37 ppm. HRMS: MHþ, found: 291.1005. C17H14OF3 requires
291.0997.
4.79. 2-(4-methoxybenzyl)-2,3-dihydro-1H-inden-1-one (6m)
Following the general procedure A, starting from enone 5m
(126 mg, 0.5 mmol), Fe (5 mg, 0.01 mmol), Me3NO (1 mg,
0.0126 mmol) and potassium formate (210 mg, 2.5 mmol) for 24 h
at 45 ꢀC, the corresponding ketone 6m was obtained as a colorless
oil (123 mg, 97%) after purification by flash column chromatog-
raphy on silica (eluent: pentane/AcOEt [90:10]); hmax (liquid film)
3030, 2931, 2835, 1705, 1609, 1585, 1511, 1463, 1433, 1324, 1294,
1272, 1244, 1207, 1177, 1151, 1108, 1092, 1032, 1002, 811, 796, 758,
4.82. 2-(4-(dimethylamino)benzyl)-2,3-dihydro-1H-inden-1-one
(6p)
Following the general procedure A, starting from enone 5p
(131 mg, 0.5 mmol), Fe (5 mg, 0.01 mmol), Me3NO (1 mg,
0.0126 mmol) and potassium formate (210 mg, 2.5 mmol) for 24 h
at 45 ꢀC, the corresponding ketone 6p was obtained as a yellow oil
(44 mg, 33%) after purification by flash column chromatography on
silica (eluent: pentane/AcOEt [90:10]); hmax (liquid film) 2916,
2849, 2800, 1705, 1676, 1610, 1519, 1463, 1444, 1433, 1340, 1293,
1273, 1207, 1164, 1151, 1115, 1093, 1060, 1042, 1001, 980, 946, 897,
824, 804, 786, 754, 727, 673, 625, 601, 555, 513 cmꢁ1.1H NMR
729, 679, 621, 602, 589, 572, 564 cmꢁ1.1H NMR (500 MHz, CDCl3)
d:
7.77 (1H, d, J ¼ 7.4 Hz), 7.57 (1H, td, J ¼ 7.0, 0.9 Hz), 7.40 (1H, d,
J ¼ 7.7 Hz), 7.36 (1H, t, J ¼ 7.4 Hz), 7.16 (2H, d, J ¼ 8.4 Hz), 6.83 (2H, d,
J ¼ 8.7 Hz), 3.79 (3H, s), 3.31 (1H, ABX, JAB ¼ 14.1 Hz, JAX ¼ 4.3 Hz),
3.16 (1H, ABX, JAB ¼ 17.2 Hz, JAX ¼ 7.8 Hz), 2.97 (1H, ABX, JAB ¼ 8 Hz,
JAX ¼ 4 Hz), 2.85 (1H, ABX, JAB ¼ 17.2 Hz, JAX ¼ 3.9 Hz), 2.65 (1H, ABX,
(500 MHz, CDCl3)
d
: 7.77 (1H, d, J ¼ 7.7 Hz), 7.56 (1H, td, J ¼ 7.4,
0.9 Hz), 7.40 (1H, d, J ¼ 7.7 Hz), 7.36 (1H, t, J ¼ 7.4 Hz), 7.12 (2H, d,
J ¼ 8.5 Hz), 6.70 (2H, d, J ¼ 8.2 Hz), 3.30 (1H, ABX, JAB ¼ 14.0 Hz,
JAX ¼ 4.3 Hz), 3.16 (1H, ABX, JAB ¼ 17.2 Hz, JAX ¼ 7.7 Hz), 2.96e2.90
(1H, m), 2.92 (6H, s), 2.88 (1H, ABX, JAB ¼ 17.2 Hz, JAX ¼ 3.9 Hz), 2.59
(1H, ABX, JAB ¼ 14.0 Hz, JAX ¼ 10.4 Hz) ppm. 13C NMR (125 MHz,
JAB ¼ 14 Hz, JAX ¼ 10.2 Hz) ppm. 13C NMR (125 MHz, CDCl3)
d: 208.1,
158.2, 153.7, 136.6, 134.8, 131.6, 129.9, 127.4, 126.6, 124.2, 113.9, 55.3,
49.2, 36.1, 32.1 ppm. HRMS: MHþ, found: 253.1232. C17H17O2 re-
quires 253.1229.
CDCl3) d: 208.3, 153.9, 136.7, 134.7, 129.6, 127.4, 126.6, 124.0, 112.9,
4.80. 2-(benzo[d][1,3]dioxol-5-ylmethyl)-2,3-dihydro-1H-inden-1-
one (6n)
49.3, 40.8, 36.1, 32.2 ppm. HRMS: MHþ, found: 266.1543. C18H20NO
requires 266.1545.
Following the general procedure A, starting from enone 5n
(132 mg, 0.5 mmol), Fe (5 mg, 0.01 mmol), Me3NO (1 mg,
0.0126 mmol) and potassium formate (210 mg, 2.5 mmol) for 24 h
at 45 ꢀC, the corresponding ketone 6n was obtained as a white
powder (111 mg, 83%) after purification by flash column chroma-
tography on silica (eluent: Pentane/AcOEt [90:10]); hmax (liquid
film) 3073, 2904, 2783, 1702, 1608, 1587, 1502, 1489, 1465, 1441,
1364, 1330, 1296, 1281, 1247, 1232, 1208, 1188, 1153, 1118, 1098,
1035, 1003, 959, 928, 898, 879, 843, 807, 789, 765, 748, 721, 685,
4.83. 2-(Furan-2-ylmethyl)-2,3-dihydro-1H-inden-1-one (6q)
Following the general procedure A, starting from enone 5q
(105 mg, 0.5 mmol), Fe (5 mg, 0.01 mmol), Me3NO (1 mg,
0.0126 mmol) and potassium formate (210 mg, 2.5 mmol) for 24 h
at 45 ꢀC, the corresponding ketone 6q was obtained as a yellow oil
(80 mg, 71%) after purification by flash column chromatography on
silica (eluent: pentane/AcOEt [90:10]); hmax (liquid film) 2918,
2848, 1706, 1607, 1506, 1464, 1431, 1382, 1328, 1293, 1277, 1207,
1181, 1148, 1093, 1075, 1042, 1010, 953, 929, 884, 798, 757, 724, 670,
641, 602, 585, 573, 549, 521 cmꢁ1.1H NMR (500 MHz, CDCl3)
d: 7.77
(1H, d, J ¼ 7.7 Hz), 7.57 (1H, td, J ¼ 7.4, 0.9 Hz), 7.41 (1H, d,
J ¼ 7.7 Hz), 7.37 (1H, t, J ¼ 7.4 Hz), 6.74 (1H, d, J ¼ 1.6 Hz), 6.73 (1H,
s), 6.68 (1H, dd, J ¼ 6.5,1.4 Hz), 5.93 (2H, s), 3.29 (1H, ABX, JAB ¼ 14.1,
4.4 Hz), 3.17 (1H, ABX, JAB ¼ 17.1 Hz, JAX ¼ 7.8 Hz), 2.94 (1H, ABX,
JAB ¼ 7.7 Hz, JAX ¼ 4.0 Hz), 2.86 (1H, ABX, JAB ¼ 17.1, JAX ¼ 4.1 Hz),
2.62 (1H, ABX, JAB ¼ 14.1 Hz, JAX ¼ 10.2 Hz) ppm. 13C NMR (125 MHz,
651, 599, 584, 552 cmꢁ1.1H NMR (500 MHz, CDCl3)
d: 7.78 (1H, d,
J ¼ 8.11 Hz), 7.58 (1H, td, J ¼ 7.5, 1.1 Hz), 7.43 (1H, dt, J ¼ 7.6, 0.8 Hz),
7.37 (1H, td, J ¼ 7.0, 0.8 Hz), 7.29 (1H, q, J ¼ 0.8 Hz), 6.27 (1H, q,
J ¼ 1.9 Hz), 6.06 (1H, q, J ¼ 0.9 Hz), 3.32 (1H, ABX, JAB ¼ 14.7 Hz,
JAX ¼ 4.5 Hz), 3.31 (1H, ABX, JAB ¼ 17.3 Hz, JAX ¼ 7.8 Hz), 3.05e2.99
(1H, m), 2.93 (1H, ABX, JAB ¼ 15.2 Hz, JBX ¼ 9.7 Hz), 2.8 (1H, ABX,
CDCl3)
d
: 207.8, 153.7, 147.7, 146.1, 136.6, 134.9, 133.4, 127.5, 126.6,
JAB ¼ 15.4 Hz, JBX ¼ 9.7 Hz). 13C NMR (125 MHz, CDCl3)
d: 207.3,
124.1, 121.9, 109.3, 108.3, 100.9, 49.1, 36.7, 32.1 ppm. HRMS: MHþ,
found: 267.1022. C17H15O3 requires 267.1021.
153.7, 153.6, 141.5, 136.4, 134.9, 127.5, 126.6, 124.1, 110.2, 106.4, 46.5,
32.5, 29.4 ppm. HRMS: MHþ, found: 213.0911. C14H13O2 requires
213.0910.
4.81. 2-(4-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-one
(6o)
4.84. 2-(Thiophen-2-ylmethyl)-2,3-dihydro-1H-inden-1-one (6r)
Following the general procedure A, starting from enone 5o
(144 mg, 0.5 mmol), Fe (5 mg, 0.01 mmol), Me3NO (1 mg,
0.0126 mmol) and potassium formate (210 mg, 2.5 mmol) for 24 h
at 45 ꢀC, the corresponding ketone 6o was obtained as a white
powder (114 mg, 79%) after purification by flash column chroma-
tography on silica (eluent: pentane/AcOEt [90:10]); hmax (liquid
film) 2918, 2852, 1696, 1607, 1584, 1466, 1444, 1427, 1325, 1296,
1207, 1196, 1185, 1163, 1150, 1110, 1066, 1017, 1005, 953, 911, 876,
811, 788, 758, 744, 729, 717, 688, 642, 628, 611, 594 cmꢁ1.1H NMR
Following the general procedure A, starting from enone 5r
(113 mg, 0.5 mmol), Fe (5 mg, 0.01 mmol), Me3NO (1 mg,
0.0126 mmol) and potassium formate (210 mg, 2.5 mmol) for 24 h
at 45 ꢀC, the corresponding ketone 6r was obtained as a white
powder (92 mg, 81%) after purification by flash column chroma-
tography on silica (eluent: pentane/AcOEt [95:5]); nmax (liquid film)
3069, 2916, 2845, 1705, 1606, 1533, 1464, 1431, 1363, 1326, 1293,
1276, 1260, 1226, 1182, 1151, 1093, 1033, 1001, 979, 952, 895, 867,
850, 824, 800, 755, 743, 722, 693, 625, 559, 540, 514 cmꢁ1.1H NMR
(500 MHz, CDCl3)
d
: 7.79 (1H, d, J ¼ 10 Hz), 7.59 (1H, td, J ¼ 7.5,
(500 MHz, CDCl3)
d
: 7.78 (1H, d, J ¼ 7.5 Hz), 7.58 (1H, td, J ¼ 7.4,
1.0 Hz), 7.56 (2H, d, J ¼ 8.1 Hz), 7.41 (1H, td, J ¼ 7.9, 0.8 Hz), 7.36 (3H,
d, J ¼ 10 Hz), 3.43 (1H, ABX, JAB ¼ 14.1 Hz, JAX ¼ 4.3 Hz), 3.20 (1H,
ABX, JAB ¼ 17.2 Hz, JAX ¼ 7.9 Hz), 3.01 (1H, ABX, JAB ¼ 7.9 Hz,
JAX ¼ 4.0 Hz), 2.83 (1H, ABX, JAB ¼ 17.2 Hz, JAX ¼ 4.2 Hz), 2.77 (1H,
1.0 Hz), 7.43 (1H, dt, J ¼ 7.7, 0.8 Hz), 7.37 (1H, td, J ¼ 7.1, 0.7 Hz), 7.13
(1H, dd, J ¼ 5.1, 1.2 Hz), 6.92 (1H, q, J ¼ 3.4, 1.6 Hz), 6.86e6.85 (1H,
m), 3.57e3.51 (1H, m), 3.31 (1H, ABX, JAB ¼ 17 Hz, JAX ¼ 7.1 Hz),
3.04e2.97 (2H, m), 2.94 (1H, ABX, JAB ¼ 17 Hz, JAX ¼ 3.5 Hz) ppm. 13
C
ABX, JAB ¼ 14.1 Hz, JAX ¼ 10.1 Hz) ppm. 13C NMR (125 MHz, CDCl3)
d
:
NMR (125 MHz, CDCl3) d: 207.2, 153.7, 142.0, 136.5, 134.9, 127.5,
14