A. Oikawa et al. / Tetrahedron 71 (2015) 1705e1711
1709
(Carom), 137.4 (2ꢂCHarom), 159.7 (Carom). IR (neat): 2954, 2925, 2869,
2852, 1587, 1494, 1458, 1276, 1242, 1180, 1074, 1035, 806 cmꢁ1
1.51e1.68 (m, 6H), 7.30e7.39 (m, 2H), 7.50e7.60 (m, 1H), 7.66e7.77
(m, 3H), 7.90e8.02 (m, 1H). 13C NMR (125 MHz, CDCl3):
9.6
.
d
(3ꢂCH2), 13.7 (3ꢂCH3), 27.4 (3ꢂCH2), 29.2 (3ꢂCH2), 125.6 (CHarom),
125.6 (CHarom), 126.8 (CHarom), 127.5 (CHarom), 127.7 (CHarom), 133.0
(CHarom), 133.4 (Carom), 133.4 (Carom), 136.5 (CHarom), 139.3 (Carom).
4.5.3. 4-Methylphenyltributylstannane (2c).14 1H NMR (500 MHz,
CDCl3):
0.88 (t, J¼7.3 Hz, 9H), 0.97e1.12 (m, 6H), 1.28e1.39 (m,
6H),1.44e1.63 (m, 6H), 2.31 (s, 3H), 7.10e7.17 (m, 2H), 7.30e7.41 (m,
2H). 13C NMR (125 MHz, CDCl3):
d
IR (neat): 2954, 2925, 2869, 2850, 1463, 812, 736 cmꢁ1
.
d
9.5 (3ꢂCH2), 13.6 (3ꢂCH3), 21.3
(CH3), 27.4 (3ꢂCH2), 29.1 (3ꢂCH2), 128.8 (2ꢂCHarom), 136.4
4.5.11. (4-Methoxyphenyl)(phenyl)methanone (3ba).9b Mp 42e43 ꢀC.
1H NMR (600 MHz, CDCl3):
3.86 (s, 3H), 6.91e6.98 (m, 2H),
7.42e7.48 (m, 2H), 7.52e7.57 (m, 1H), 7.72e7.77 (m, 2H), 7.79e7.85
(m, 2H). 13C NMR (150 MHz, CDCl3):
(2ꢂCHarom), 137.5 (Carom), 137.7 (Carom). IR (neat): 2956, 2923, 2869,
d
2852, 1456, 1068, 790 cmꢁ1
.
d
55.4 (CH3), 113.5 (2ꢂCHarom),
4.5.4. 2-Methylphenyltributylstannane (2d).3b 1H NMR (500 MHz,
CDCl3):
0.88 (t, J¼7.3 Hz, 9H), 1.01e1.16 (m, 6H), 1.29e1.38 (m, 6H),
1.45e1.62 (m, 6H), 2.38 (s, 3H), 7.06e7.22 (m, 3H), 7.32e7.44 (m,
1H). 13C NMR (125 MHz, CDCl3):
128.1 (2ꢂCHarom), 129.7 (2ꢂCHarom), 130.1(Carom), 131.8 (CHarom),
132.5 (2ꢂCHarom), 138.2 (Carom), 163.2 (Carom), 195.4 (C]O). IR (neat):
1651, 1598, 1573, 1504, 1446, 1417, 1280, 1257, 1172, 1149, 1029, 937,
d
d
10.0 (3ꢂCH2), 13.6 (3ꢂCH3), 24.9
921, 844, 792, 740, 702, 599 cmꢁ1
.
(CH3), 27.4 (3ꢂCH2), 29.2 (3ꢂCH2), 124.8 (CHarom), 128.2 (CHarom),
128.8 (CHarom), 136.4 (CHarom), 141.7 (Carom), 144.4 (Carom). IR (neat):
4.5.12. (4-Methylphenyl)(phenyl)methanone (3ca).18 Mp 47e48 ꢀC.
1H NMR (500 MHz, CDCl3):
2.36 (s, 3H), 7.20e7.24 (m, 2H),
7.39e7.43 (m, 2H), 7.49e7.53 (m, 1H), 7.67e7.70 (m, 2H), 7.73e7.76
(m, 2H). 13C NMR (125 MHz, CDCl3):
2956, 2925, 2869, 2852, 1458, 1375, 740 cmꢁ1
.
d
4.5.5. 4-Fluorophenyltributylstannane (2e).2n 1H NMR (500 MHz,
CDCl3):
0.88 (t, J¼7.3 Hz, 9H), 0.98e1.14 (m, 6H),1.28e1.38 (m, 6H),
1.46e1.63 (m, 6H), 6.95e7.03 (m, 2H), 7.34e7.46 (m, 2H). 13C NMR
(125 MHz, CDCl3):
d
21.3 (CH3), 127.9 (2ꢂCHarom),
d
128.6 (2ꢂCHarom), 129.5 (2ꢂCHarom), 129.9 (2ꢂCHarom), 131.8
(CHarom), 134.5 (Carom), 137.5 (Carom), 142.8 (Carom), 195.9 (C]O). IR
(neat): 1645, 1604, 1448, 1319, 1276, 937, 920, 839, 788, 738, 700,
d
9.6 (3ꢂCH2), 13.6 (3ꢂCH3), 27.4 (3ꢂCH2), 29.1
(3ꢂCH2), 115.1 (d, J¼18.6 Hz, 2ꢂCHarom), 136.5 (d, J¼4.1 Hz, Carom),
137.8 (d, J¼7.2 Hz, 2ꢂCHarom), 163.3 (d, J¼247.2 Hz, Carom). IR (neat):
599 cmꢁ1
.
2956, 2925, 2871, 2852,1581,1490,1463,1228,1163,1062, 815 cmꢁ1
.
4.5.13. (2-Methylphenyl)(phenyl)methanone
(500 MHz, CDCl3): 2.30 (s, 3H), 7.15e7.20 (m, 1H), 7.21e7.27 (m,
2H), 7.30e7.34 (m, 1H), 7.35e7.40 (m, 2H), 7.47e7.51 (m, 1H),
7.76e7.80 (m, 2H). 13C NMR (125 MHz, CDCl3):
19.6 (CH3), 124.8
(3da).9h 1H
NMR
d
4.5.6. 2-Bromophenyltributylstannane (2f).15 1H NMR (500 MHz,
CDCl3):
d
0.88 (t, J¼7.3 Hz, 9H), 1.09e1.24 (m, 6H), 1.29e1.38 (m,
d
6H), 1.47e1.65 (m, 6H), 7.06e7.12 (m, 1H), 7.16e7.22 (m, 1H),
(CHarom), 128.0 (2ꢂCHarom), 128.1 (CHarom), 129.6 (2ꢂCHarom), 129.8
(CHarom), 130.6 (CHarom), 132.7 (CHarom), 136.3 (Carom), 137.3 (Carom),
138.2 (Carom), 197.9 (C]O). IR (neat): 1666, 1596, 1579, 1448, 1315,
7.25e7.36 (m, 1H), 7.42e7.48 (m, 1H). 13C NMR (125 MHz, CDCl3):
d
10.8 (3ꢂCH2), 13.6 (3ꢂCH3), 27.3 (3ꢂCH2), 29.0 (3ꢂCH2), 126.2
(CHarom), 129.8 (CHarom), 131.6 (CHarom), 133.3 (Carom), 137.9
(CHarom), 146.5 (Carom). IR (neat): 2954, 2922, 2869, 2852, 1463,
1290, 1267, 1153, 923, 763, 732, 709, 698, 640 cmꢁ1
.
1413, 1245, 1085, 1006, 746 cmꢁ1
.
4.5.14. (4-Fluorophenyl)(phenyl)methanone
(600 MHz, CDCl3): 7.05e7.12 (m, 2H), 7.39e7.45 (m, 2H),
7.49e7.55 (m, 1H), 7.70e7.75 (m, 2H), 7.76e7.81 (m, 2H). 13C NMR
(150 MHz, CDCl3):
(3ea).9n 1H
NMR
d
4.5.7. 3-Acetylphenyltributylstannane (2g).3b 1H NMR (500 MHz,
CDCl3):
d
0.89 (t, J¼7.3 Hz, 9H), 1.04e1.20 (m, 6H), 1.30e1.40 (m,
d
112.9 (d. J¼22.1 Hz, 2ꢂCHarom), 125.9
6H), 1.47e1.66 (m, 6H), 2.56 (s, 3H), 7.32e7.42 (m, 1H), 7.60e7.71
(2ꢂCHarom), 127.4 (2ꢂCHarom), 130.0(CHarom), 130.2 (d, J¼9.6 Hz,
2ꢂCHarom), 131.3 (d, J¼2.8 Hz, Carom), 135.0 (Carom), 162.8 (d,
J¼254.0 Hz, Carom), 192.4 (C]O). IR (neat): 1660, 1598, 1504, 1301,
(m, 1H), 7.79e7.88 (m, 1H), 8.09 (s, 1H). 13C NMR (125 MHz, CDCl3):
d
9.3 (3ꢂCH2),13.3 (3ꢂCH3), 26.1 (CH3), 27.0 (3ꢂCH2), 28.8 (3ꢂCH2),
127.6 (CHarom), 127.7 (CHarom), 135.6 (CHarom), 136.0 (Carom), 140.8
1276, 1228, 1155, 923, 850, 736, 700, 599 cmꢁ1
.
(CHarom), 142.4 (Carom), 198.0 (C]O). IR (neat): 2956, 2925, 2869,
2852, 1685, 1463, 1355, 1255, 790, 696 cmꢁ1
.
4.5.15. (3-Acetylphenyl)(phenyl)methanone
(600 MHz, CDCl3): 2.69 (s, 3H), 7.46e7.51 (m, 2H), 7.56e7.62 (m,
2H), 7.78 (d, J¼8.2 Hz, 2H), 7.96 (d, J¼7.6 Hz, 1H), 8.17 (d, J¼7.6 Hz,
1H), 8.36 (s, 1H). 13C NMR (150 MHz, CDCl3):
26.6 (CH3), 128.4
(3ga).9n 1H
NMR
d
4.5.8. 3-Nitrophenyltributylstannane (2h).3d 1H NMR (600 MHz,
CDCl3):
d
0.89 (t, J¼7.5 Hz, 9H), 1.07e1.20 (m, 6H), 1.30e1.38 (m,
d
6H), 1.47e1.62 (m, 6H), 7.45e7.51 (m, 1H), 7.73e7.82 (m, 1H),
(2ꢂCHarom), 128.7 (CHarom), 129.5 (CHarom), 129.9 (2ꢂCHarom), 131.7
(CHarom), 132.8 (CHarom), 134.1 (CHarom), 136.9 (Carom), 137.0 (Carom),
137.9(Carom), 195.6 (C]O), 197.1 (C]O). IR (neat): 1681, 1660, 1598,
1446, 1427, 1357, 1286, 1242, 1145, 968, 779, 719, 700, 646,
8.10e8.15 (m, 1H), 8.26e8.34 (m, 1H). 13C NMR (150 MHz, CDCl3):
d
9.8 (3ꢂCH2), 13.6 (3ꢂCH3), 27.3 (3ꢂCH2), 28.9 (3ꢂCH2), 122.9
(CHarom), 128.4 (CHarom), 130.4 (CHarom), 142.5 (CHarom), 144.9
(Carom), 147.7 (Carom). IR (neat): 2956, 2925, 2871, 2852, 1523, 1463,
594 cmꢁ1
.
1344, 864, 727, 680 cmꢁ1
.
4.5.16. (3-Nitrophenyl)(phenyl)methanone (3ha).9a Mp 94e95 ꢀC.
1H NMR (600 MHz, CDCl3):
4.5.9. 1-Naphthyltributylstannane (2i).16 1H NMR (500 MHz,
CDCl3):
d
7.53 (t, J¼7.6 Hz, 2H), 7.65 (t, J¼7.6 Hz,
d
0.85 (t, J¼7.3 Hz, 9H),1.13e1.28 (m, 6H),1.29e1.38 (m, 6H),
1H), 7.71 (t, J¼7.6 Hz, 1H), 7.79 (d, J¼8.2 Hz, 2H), 8.14 (d, J¼6.8 Hz,
1.49e1.66 (m, 6H), 7.30e7.38 (m, 2H), 7.40e7.45 (m, 1H), 7.61e7.65
1H), 8.44 (d, J¼8.3 Hz, 1H), 8.61 (s, 1H). 13C NMR (150 MHz, CDCl3):
(m, 1H), 7.67e7.75 (m, 2H), 7.78e7.82 (m, 1H). 13C NMR (125 MHz,
d
124.6 (CHarom), 126.7 (CHarom), 128.7 (2ꢂCHarom), 129.6 (CHarom),
CDCl3):
d
10.4 (3ꢂCH2), 13.6 (3ꢂCH3), 27.4 (3ꢂCH2), 29.2 (3ꢂCH2),
130.0 (2ꢂCHarom), 133.3 (CHarom), 135.4 (CHarom), 136.2 (Carom),
139.0 (Carom), 148.0 (Carom), 194.1 (C]O).
125.3 (CHarom), 125.3 (CHarom), 125.6 (CHarom), 128.5 (CHarom), 128.9
(CHarom), 130.1 (CHarom), 133.8 (Carom), 135.1 (CHarom), 139.1 (Carom),
142.7 (Carom). IR (neat): 3049, 2954, 2925, 2869, 2852, 1500, 1463,
4.5.17. (1-Naphthyl)(phenyl)methanone (3ia).19 1H NMR (600 MHz,
1375, 790, 773 cmꢁ1
.
CDCl3):
d
7.31e7.51 (m, 7H), 7.79e7.84 (m, 3H), 7.88e7.91 (m, 1H),
124.2 (CHarom),
8.08e8.12 (m, 1H). 13C NMR (150 MHz, CDCl3):
d
4.5.10. 2-Naphthyltributylstannane (2j).17 1H NMR (500 MHz,
CDCl3):
0.89 (t, J¼7.3 Hz, 9H),1.06e1.22 (m, 6H),1.31e1.41 (m, 6H),
125.5 (CHarom), 126.3 (CHarom), 127.1 (CHarom), 127.6 (CHarom), 128.2
(CHarom), 128.3 (2ꢂCHarom), 130.2 (2ꢂCHarom), 130.8 (Carom), 131.1
d