6738
J. Ma et al. / Tetrahedron 71 (2015) 6733e6739
until the reaction was completed. The autoclave was taken out from
the oil bath, cooled to room temperature and carefully depressur-
ized. The mixture was concentrated under reduced pressure and
purified by column chromatography to give the desired
diarylketones.
129.2, 128.6, 21.7; MS (EI), m/z 229.91 [Mþ, 28%], 119.05 (100%),
calcd for C14H11ClO¼230.05.
3.2.10. (4-Chlorophenyl)(4-methoxyphenyl)methanone
(2j).22 White solid; mp: 124e125 ꢀC (lit.20 116e118 ꢀC); 1H NMR
(500 MHz, CDCl3)
d
7.83e7.80 (m, 4H), 7.17 (t, J¼8.7 Hz, 2H),
3.2.1. Benzophenone (2a).8d,9 White solid; mp: 48e49 ꢀC (lit.19
7.00e6.98 (m, 2H), 3.91 (s, 3H); 13C NMR (125 MHz, CDCl3)
d
194.3,
46e47.5 ꢀC); 1H NMR (500 MHz, CDCl3)
d
7.81e7.80 (m, 4H),
7.61e7.58 (m, 2H), 7.50e7.47 (m, 4H); 13C NMR (125 MHz, CDCl3)
196.7, 137.6, 132.4, 130.1, 128.3; MS (EI), m/z 182.10 [Mþ, 36%],
163.4, 138.3, 136.6, 132.4, 131.1, 129.8, 128.5, 113.7, 55.5; MS (EI), m/z
246.02 [Mþ, 25%], 135.05 (100%), calcd for C14H11ClO2¼246.04.
d
105.06 (100%), calcd for C13H10O¼182.07.
3.2.11. (4-Fluorophenyl)(4-methoxyphenyl)methanone
(2k).21 White solid; mp: 94e95 ꢀC (lit.20 89e91 ꢀC);1H NMR
3.2.2. Phenyl(o-tolyl)methanone (2b).6a Colorless oil; 1H NMR
(500 MHz, CDCl3)
d 7.82e7.81 (m, 2H), 7.73e7.71 (m, 2H), 7.48e7.46
(500 MHz, CDCl3)
d 7.83e7.81 (m, 2H), 7.61e7.59 (m, 1H), 7.49e7.46
(m, 2H), 7.00e6.98 (m, 2H), 3.91 (s, 3H); 13C NMR (125 MHz, CDCl3)
(m, 2H), 7.43e7.40 (m, 1H), 7.34e7.25 (m, 3H), 2.35 (s, 3H); 13C NMR
d
194.1, 165.1 (d, J¼251.6 Hz), 163.3, 134.5 (d, J¼2.6 Hz), 132.5, 132.3
(125 MHz, CDCl3)
d
198.6, 138.6, 137.8, 136.7, 133.1, 131.0, 130.3,
(d, J¼9.1 Hz), 130.1, 115.4 (d, J¼21.7 Hz), 113.7, 55.6; MS (EI), m/z
130.1, 128.52, 128.48, 125.2, 20.0; MS (EI), m/z 196.10 [Mþ, 70%],
195.01 (100%), calcd for C14H12O¼196.09.
230.06 [Mþ, 35%], 135.05 (100%), calcd for C14H11FO2¼230.07.
3.2.12. 9H-Fluoren-9-one (2l).8c,8d,11b White solid; mp: 83e84 ꢀC
3.2.3. Phenyl(m-tolyl)methanone (2c).6a Colorless oil; 1H NMR
(lit.19 79e82 ꢀC); 1H NMR (500 MHz, CDCl3)
d
7.63 (d, J¼7.4 Hz, 2H),
(500 MHz, CDCl3)
d 7.83e7.81 (m, 2H), 7.65 (s, 1H), 7.62e7.59 (m,
7.48e7.43 (m, 4H), 7.28e7.25 (m, 2H); 13C NMR (125 MHz, CDCl3)
2H), 7.51e7.48 (m, 2H), 7.43e7.36 (m, 2H), 2.44 (s, 3H); 13C NMR
d
193.7, 144.4, 134.6, 134.1, 129.0, 124.2, 120.2. MS (EI), m/z 179.98
(125 MHz, CDCl3)
d
197.0, 138.2, 137.8, 137.7, 133.2, 132.4, 130.5,
[Mþ, 100%], calcd for C13H8O¼180.06.
130.0, 128.3, 128.1, 127.4, 21.4; MS (EI), m/z 196.13 [Mþ, 60%], 119.01
(100%), calcd for C14H12O¼196.09.
3.2.13. Biphenyl-4-yl(phenyl)methanone (2m).10 White solid; mp:
100e101 ꢀC (lit.23 98e99 ꢀC); 1H NMR (500 MHz, CDCl3)
d 7.93e7.91
3.2.4. Phenyl(p-tolyl)methanone (2d).6a,9 Colorless oil; 1H NMR
(m, 2H), 7.87e7.85 (m, 2H), 7.74e7.72 (m, 2H), 7.68e7.66 (m, 2H),
(500 MHz, CDCl3)
d
7.81e7.79 (m, 2H), 7.74 (d, J¼8.2 Hz, 2H),
7.64e7.61 (m, 1H), 7.54e7.49 (m, 4H), 7.45e7.41 (m, 1H); 13C NMR
7.61e7.58 (m,1H), 7.51e7.48 (m, 2H), 7.31e7.28 (m, 2H), 2.46 (s, 3H).
(125 MHz, CDCl3)
d 196.4, 145.3, 140.1, 137.9, 136.3, 132.4, 130.8,
13C NMR (125 MHz, CDCl3)
d
196.5, 143.2, 138.0, 134.9, 132.2, 130.3,
130.1,129.0,128.4,128.2,127.4,127.0; MS (EI), m/z 258.08 [Mþ, 70%],
181.00 (100%), calcd for C19H14O¼258.10.
129.9, 129.0, 128.2, 21.6; MS (EI), m/z 196.09 [Mþ, 45%], 119.00
(100%), calcd for C14H12O¼196.09.
3.2.14. Biphenyl-4-yl(4-methoxyphenyl)methanone (2n).24 White
3.2.5. (4-Methoxyphenyl)(phenyl)methanone (2e).5a,5b Colorless oil;
solid; mp: 87e88 ꢀC. 1H NMR (500 MHz, CDCl3)
d 7.90e7.86 (m, 4H),
1H NMR (500 MHz, CDCl3)
d
7.86e7.83 (m, 2H), 7.78e7.76 (m, 2H),
7.73e7.71 (m, 2H), 7.68e7.66 (m, 2H), 7.52e7.49 (m, 2H), 7.44e7.42
7.60e7.57 (m, 1H), 7.50e7.47 (m, 2H), 7.00e6.97 (m, 2H), 3.91 (s,
(m, 1H), 7.02e7.00 (m, 2H), 3.92 (s, 3H); 13C NMR (125 MHz, CDCl3)
3H); 13C NMR (125 MHz, CDCl3)
d
195.5, 163.2, 138.3, 132.5, 131.9,
d 195.2, 163.2, 144.7, 140.1, 136.9, 132.5, 130.4, 130.3, 128.9, 128.1,
130.2, 129.7, 128.2, 113.6, 55.5; MS (EI), m/z 212.11 [Mþ, 38%], 134.96
(100%), calcd for C14H12O2¼212.08.
127.3, 126.9, 113.6, 55.5; MS (EI), m/z 288.06 [Mþ, 40%], 135.02
(100%), calcd for C20H16O2¼288.12.
3.2.6. (3-Methoxyphenyl)(phenyl)methanone (2f).6e Colorless oil;
3.2.15. (4-Methoxyphenyl)(naphthalen-1-yl)methanone
1H NMR (500 MHz, CDCl3)
d
7.83e7.82 (m, 2H), 7.62e7.59 (m, 1H),
(2o).25 White solid; mp: 94e95 ꢀC (lit.26 97 ꢀC); 1H NMR (500 MHz,
7.51e7.48 (m, 2H), 7.41e7.35 (m, 3H), 7.15e7.14 (m, 1H), 3.88 (s, 3H);
CDCl3)
d
8.02e7.86 (m, 5H), 7.58e7.48 (m, 4H), 6.95e6.94 (m, 2H),
196.7, 163.9, 137.1, 133.7,
13C NMR (125 MHz, CDCl3):
d
196.5, 159.6, 138.9, 137.6, 132.4, 130.0,
3.89 (s, 3H); 13C NMR (125 MHz, CDCl3)
d
129.2, 128.3, 122.8, 118.8, 114.4, 55.4; MS (EI), m/z 212.12 [Mþ, 82%],
105.00 (100%), calcd for C14H12O2¼212.08.
132.8, 131.1, 130.9, 130.7, 128.4, 127.1, 126.9, 126.4, 125.7, 124.5, 113.8,
55.5; MS (EI), m/z 262.14 [Mþ, 70%], 135.04 (100%), calcd for
C18H14O2¼262.10.
3.2.7. (4-Fluorophenyl)(phenyl)methanone (2g).6a,9 White solid;
mp: 94e95 ꢀC (lit.20 45e47 ꢀC); 1H NMR (500 MHz, CDCl3)
3.2.16. Naphthalen-1-yl(phenyl)methanone (2p).6a,10 White solid;
d
7.80e7.77 (m, 4H), 7.62e7.60 (m, 1H), 7.52e7.47 (m, 4H); 13C NMR
mp: 72e73 ꢀC (lit.10 75e76 ꢀC); 1H NMR (500 MHz, CDCl3)
8.11 (d,
J¼8.2 Hz, 1H), 8.03 (d, J¼8.2 Hz, 1H), 7.96e7.94 (m, 1H), 7.90e7.88
(m, 2H), 7.64e7.28 (m, 7H); 13C NMR (125 MHz, CDCl3)
198.0,
d
(125 MHz, CD3Cl3)
d
195.2, 165.4 (d, J¼252.4 Hz), 137.5, 133.8 (d,
J¼3.3 Hz), 132.7 (d, J¼9.1 Hz), 132.5, 129.9, 128.4, 115.4 (d,
d
J¼21.8 Hz); MS (EI), m/z 199.93 [Mþ, 83%], 123.07 (100%), calcd for
138.3, 136.4, 133.7, 133.2, 131.3, 131.0, 130.4, 128.45, 128.41, 127.8,
127.3, 126.5, 125.7, 124.3; MS (EI), m/z 232.12 [100%], calcd for
C
13H9FO¼200.06.
C17H12O¼232.09.
3.2.8. (4-Chlorophenyl)(phenyl)methanone (2h).6a,9,21 White solid;
mp: 72e73 ꢀC (lit.20 74e76 ꢀC); 1H NMR (500 MHz, CDCl3)
3.2.17. Phenyl(pyridin-4-yl)methanone (2q).27 Colorless oil; 1H
d
7.78e7.75 (m, 4H), 7.62e7.59 (m, 1H), 7.51e7.46 (m, 4H); 13C NMR
NMR (500 MHz, CDCl3) 8.84e8.83 (m, 2H), 7.85e7.83 (m, 2H),
7.69e7.65 (m, 1H), 7.61e7.60 (m, 2H), 7.55e7.52 (m, 2H); 13C NMR
(125 MHz, CDCl3) 195.2, 150.4, 144.4, 136.0, 133.6, 130.2, 128.7,
122.9; MS (EI), m/z 183.07 [Mþ, 40%], 105.07 (100%), calcd for
12H9NO¼183.07.
d
(125 MHz, CDCl3)
128.6, 128.4; MS (EI), m/z 216.07 [Mþ, 50%], 105.04 (100%), calcd for
13H9ClO¼216.03.
d 195.5, 138.9, 137.3, 135.9, 132.6, 131.5, 129.9,
d
C
C
3.2.9. (4-Chlorophenyl)(p-tolyl)methanone (2i).22 Colorless oil; 1H
NMR (500 MHz, CDCl3)
d
7.76e7.74 (m, 2H), 7.71 (d, J¼8.1 Hz, 2H),
3.2.18. (4-Methoxyphenyl)(pyridin-4-yl)methanone (2r).24 Brown
solid; mp: 119e120 ꢀC; 1H NMR (500 MHz, CDCl3)
8.81 (d,
J¼3.9 Hz, 2H), 7.84 (d, J¼8.9 Hz, 2H), 7.56 (d, J¼5.7 Hz, 2H), 7.00 (d,
7.48e7.46 (m, 2H), 7.31 (d, J¼8.0 Hz, 2H), 2.46 (s, 3H); 13C NMR
d
(125 MHz, CDCl3)
d 195.3, 143.6, 138.7, 136.3, 134.6, 131.4, 130.2,