The Journal of Organic Chemistry
Article
F
13
1
MHz, CDCl ): δ 173.8, 173.6, 140.2, 132.9 (q, J = 32.7 Hz), 128.1,
7.29−7.23 (m, 2H). C{ H} NMR (126 MHz, CDCl ): δ 165.4,
3
3
F
F
1
25.5 (q, J = 3.8 Hz), 124.0 (q, J = 272.9 Hz), 46.4, 35.0, 23.0, 21.6.
151.2, 133.8, 130.4, 129.9, 129.8, 128.8, 126.2, 122.0.
S-Phenyl Benzothioate (10). Yield: 83% (1.78 g). White solid.
19
F NMR (471 MHz, CDCl ): δ −62.97 (s).
3
1
Methyl 4-(2-Oxopiperidine-1-carbonyl)benzoate (2e). Yield:
0% (0.36 g). White solid. Mp: 119−120 °C. H NMR (500 MHz,
CDCl ): δ 8.05 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.5 Hz, 2H), 3.92 (s,
H NMR (500 MHz, CDCl ): δ 8.10−8.02 (m, 2H), 7.62 (t, J = 7.4
3
13 1
1
7
Hz, 1H), 7.55 (dt, J = 5.3, 2.0 Hz, 2H), 7.53−7.46 (m, 5H). C{ H}
NMR (126 MHz, CDCl
129.0, 127.8, 127.7.
): δ 190.4, 136.9, 135.4, 134.0, 129.8, 129.5,
3
3
3
4
1
H), 3.82 (t, J = 5.8 Hz, 2H), 2.56 (t, J = 6.6 Hz, 2H), 2.01−1.92 (m,
4a
H). 13C{ H} NMR (126 MHz, CDCl ): δ 174.0, 173.7, 166.6, 140.8,
1
All products reported here have been previously reported: 12a,
3
4a
9h
9h
9h
9h
30
9h
27
27
27
32.5, 129.8, 127.7, 52.6, 46.3, 35.0, 23.1, 21.7. HRMS (ESI): m/z [M
H] calcd for C H NO 262.1074, found 262.1074.
-(2-Methylbenzoyl)piperidin-2-one (2f). Yield: 73% (0.79 g).
Colorless oil. H NMR (500 MHz, CDCl ): δ 7.17−7.12 (m, 1H),
.07 (d, J = 7.8 Hz, 1H), 7.04 (d, J = 3.7 Hz, 2H), 3.70 (t, J = 6.0 Hz,
H), 2.33 (t, J = 6.7 Hz, 2H), 2.23 (s, 3H), 1.80−1.69 (m, 4H).
C{ H} NMR (126 MHz, CDCl ): δ 173.8, 172.7, 138.0, 134.5,
12b, 12c, 12d, 12e, 12f, 12g, 12h, 12i, 12j, 12k,
27 27 27 27 4a 4a 29
+
+
12l, 12m, 12n, 12o, 12p, 12q, and 12r. Spectroscopic
data matched those reported in the literature.
14
16
4
1
1
Phenyl(p-tolyl)methanone (12a). According to the general
procedure, the reaction of 1-benzoylpiperidin-2-one (20.3 mg, 0.10
mmol, 1.0 equiv) and p-tolylboronic acid (27.2 mg, 0.20 mmol, 2.0
equiv) afforded the title compound after workup and chromatog-
raphy. Yield: 89% (17.4 mg). White solid. H NMR (500 MHz,
CDCl ): δ 7.79 (d, J = 7.3 Hz, 2H), 7.73 (d, J = 8.1 Hz, 2H), 7.57 (t, J
7.4 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.28 (d, J = 7.8 Hz, 2H), 2.44
(s, 3H). C{ H} NMR (126 MHz, CDCl ): δ 196.8, 143.5, 138.3,
35.2, 132.4, 130.6, 130.2, 129.3, 128.5, 21.9.
Di-p-tolylmethanone (12b). According to the general procedure,
the reaction of 1-(4-methylbenzoyl)piperidin-2-one (21.7 mg, 0.10
mmol, 1.0 equiv) and p-tolylboronic acid (27.2 mg, 0.20 mmol, 2.0
equiv) afforded the title compound after workup and chromatog-
raphy. Yield: 95% (19.9 mg). White solid. H NMR (500 MHz,
CDCl ): δ 7.73 (d, J = 8.1 Hz, 4H), 7.30 (d, J = 7.9 Hz, 4H), 2.46 (s,
6H). C{ H} NMR (126 MHz, CDCl
29.2, 21.9.
4-Methoxyphenyl)(p-tolyl)methanone (12c). According to
the general procedure, the reaction of 1-(4-methoxybenzoyl)-
piperidin-2-one (23.3 mg, 0.10 mmol, 1.0 equiv) and p-tolylboronic
acid (27.2 mg, 0.20 mmol, 2.0 equiv) afforded the title compound
3
7
2
1
3
1
3
1
1
30.4, 129.3, 125.6, 125.4, 44.9, 34.5, 22.6, 20.9, 19.4. HRMS (ESI):
m/z [M + H] calcd for C H NO 218.1176, found 218.1174.
+
3
1
3
16
2
=
1
-([1,1′-Biphenyl]-4-carbonyl)piperidin-2-one (2g). Yield:
1
3
1
1
3
7
0% (0.39 g). White solid. Mp: 147−148 °C. H NMR (500 MHz,
1
CDCl ): δ 7.68−7.55 (m, 6H), 7.45 (t, J = 7.6 Hz, 2H), 7.37 (t, J =
3
7
1
.3 Hz, 1H), 3.83 (t, J = 5.7 Hz, 2H), 2.60 (t, J = 6.5 Hz, 2H), 2.03−
.94 (m, 4H). 1 C{ H} NMR (126 MHz, CDCl ): δ 174.8, 173.9,
3
1
3
1
2
44.8, 140.6, 135.1, 129.2, 128.9, 128.2, 127.6, 127.2, 46.6, 35.0, 23.2,
+
1.8. HRMS (ESI): m/z [M + H] calcd for C H NO 280.1332,
1
8
18
2
1
found 280.1329.
3
1
-(Furan-2-carbonyl)piperidin-2-one (2h). Yield: 72% (0.56
g). White solid. Mp: 58−59 °C. H NMR (500 MHz, CDCl ): δ 7.44
d, J = 0.8 Hz, 1H), 7.10 (d, J = 3.5 Hz, 1H), 6.46 (dd, J = 3.5, 1.7 Hz,
1
3
1
1
3
): δ 196.5, 143.2, 135.5, 130.5,
3
1
(
(
1
1
1
H), 3.71 (t, J = 4.5 Hz, 2H), 2.57 (dd, J = 8.3, 4.9 Hz, 2H), 1.93−
.90 (m, 4H). 13C{ H} NMR (126 MHz, CDCl ): δ 173.4, 163.8,
1
3
48.7, 145.3, 117.9, 112.2, 46.4, 34.8, 23.0, 21.9. HRMS (ESI): m/z
M + H] calcd for C H NO 194.0812, found 194.0812.
-Benzoylpyrrolidine-2,5-dione (3). Yield: 75% (1.52 g). White
solid. H NMR (500 MHz, CDCl ): δ 7.84 (d, J = 7.3 Hz, 2H), 7.65
t, J = 7.5 Hz, 1H), 7.49 (t, J = 7.9 Hz, 2H), 2.91 (s, 4H). C{ H}
NMR (126 MHz, CDCl ): δ 175.0, 168.0, 135.4, 131.7, 130.8, 129.3,
+
[
1
1
0
12
3
after workup and chromatography. Yield: 96% (21.7). White solid. H
NMR (500 MHz, CDCl ): δ 7.83 (d, J = 8.9 Hz, 2H), 7.70 (d, J = 8.1
1
1
3
3
Hz, 2H), 7.29 (d, J = 8.0 Hz, 2H), 6.98 (d, J = 8.9 Hz, 2H), 3.90 (s,
1
3
1
(
13
1
3
H), 2.46 (s, 3H). C{ H} NMR (126 MHz, CDCl ): δ 195.6,
3
3
1
63.4, 142.9, 135.8, 132.7, 130.8, 130.3, 129.2, 113.8, 55.8, 21.9.
p-Tolyl[4-(trifluoromethyl)phenyl]methanone (12d). Accord-
ing to the general procedure, the reaction of 1-[4-(trifluoromethyl)-
benzoyl]piperidin-2-one (27.1 mg, 0.10 mmol, 1.0 equiv) and p-
tolylboronic acid (27.2 mg, 0.20 mmol, 2.0 equiv) afforded the title
compound after workup and chromatography. Yield: 96% (25.3 mg).
White solid. H NMR (500 MHz, CDCl ): δ 7.87 (d, J = 8.1 Hz, 2H),
.73 (dd, J = 13.5, 8.1 Hz, 4H), 7.31 (d, J = 7.9 Hz, 2H), 2.46 (s, 3H).
C{ H} NMR (126 MHz, CDCl ): δ 195.6, 144.4, 141.5, 134.4,
2
9.4.
2
-Benzoylisoindoline-1,3-dione (4). Yield: 80% (2.00 g). White
solid. H NMR (500 MHz, CDCl ): δ 8.03−7.95 (m, 2H), 7.91−7.83
m, 4H), 7.66 (t, J = 7.5 Hz, 1H), 7.50 (t, J = 7.8 Hz, 2H). C{ H}
1
3
1
3
1
(
NMR (126 MHz, CDCl ): δ 167.4, 165.9, 135.6, 134.8, 132.9, 131.8,
3
1
30.8, 129.0, 124.8.
1
3
1
-Benzoylpyrrolidin-2-one (5). Yield: 62% (0.59 g). White
solid. H NMR (500 MHz, CDCl ): δ 7.60 (d, J = 7.2 Hz, 2H), 7.51
7
1
13
1
3
3
(
2
t, J = 7.5 Hz, 1H), 7.40 (t, J = 7.7 Hz, 2H), 3.95 (t, J = 7.1 Hz, 2H),
F
F
1
1
33.9 (q, J = 32.7 Hz), 130.7, 130.4, 129.6, 125.6 (q, J = 3.7 Hz),
24.1 (q, J = 273.1 Hz), 22.1. F NMR (471 MHz, CDCl ): δ
1
3
1
.59 (t, J = 8.0 Hz, 2H), 2.16−2.10 (m, 2H). C{ H} NMR (126
F
19
3
MHz, CDCl ): δ 174.8, 171.0, 134.7, 132.2, 129.2, 128.1, 46.8, 33.6,
3
−62.97 (s).
1
7.9.
3
Methyl 4-(4-Methylbenzoyl)benzoate (12e). According to the
general procedure, the reaction of methyl 4-(2-oxopiperidine-1-
carbonyl)benzoate (26.1 mg, 0.10 mmol, 1.0 equiv) and p-
tolylboronic acid (27.2 mg, 0.20 mmol, 2.0 equiv) afforded the title
compound after workup and chromatography. Yield: 93% (23.6 mg).
White solid. H NMR (500 MHz, CDCl ): δ 8.14 (d, J = 8.5 Hz, 2H),
-Benzoyloxazolidin-2-one (6). Yield: 77% (0.74 g). White
solid. H NMR (500 MHz, CDCl ): δ 7.66 (d, J = 7.2 Hz, 2H), 7.55
t, J = 7.5 Hz, 1H), 7.43 (t, J = 7.7 Hz, 2H), 4.47 (t, J = 7.8 Hz, 2H),
.16 (t, J = 7.8 Hz, 2H). C{ H} NMR (126 MHz, CDCl ): δ 170.1,
1
3
(
4
1
3
1
3
1
53.5, 132.9, 132.7, 129.4, 128.2, 62.6, 44.0.
1
3
3
-Benzoylbenzo[d]oxazol-2(3H)-one (7). Yield: 75% (0.90 g).
7
.81 (d, J = 8.5 Hz, 2H), 7.71 (d, J = 8.1 Hz, 2H), 7.30 (d, J = 7.9 Hz,
2H), 3.96 (s, 3H), 2.45 (s, 3H). C{ H} NMR (126 MHz, CDCl ):
1
White solid. H NMR (500 MHz, CDCl ): δ 7.88−7.84 (m, 1H),
13
1
3
3
7
7
1
1
.84−7.77 (m, 2H), 7.65 (t, J = 7.5 Hz, 1H), 7.51 (t, J = 7.8 Hz, 2H),
δ 196.1, 166.7, 144.2, 142.1, 134.6, 133.4, 130.7, 130.0, 129.8, 129.5,
52.8, 22.0.
o-Tolyl(p-tolyl)methanone (12f). According to the general
procedure, the reaction of 1-(2-methylbenzoyl)piperidin-2-one (20.3
mg, 0.10 mmol, 1.0 equiv) and p-tolylboronic acid (27.2 mg, 0.20
mmol, 2.0 equiv) afforded the title compound after workup and
chromatography. Yield: 94% (19.7 mg). White solid. H NMR (500
MHz, CDCl ): δ 7.74 (d, J = 8.2 Hz, 2H), 7.40 (td, J = 7.5, 1.4 Hz,
1H), 7.34−7.24 (m, 5H), 2.45 (s, 3H), 2.35 (s, 3H). C{ H} NMR
(126 MHz, CDCl ): δ 198.7, 144.4, 139.3, 136.8, 135.5, 131.2, 130.6,
1
3
1
.31−7.25 (m, 3H). C{ H} NMR (126 MHz, CDCl ): δ 168.1,
3
51.3, 143.1, 133.9, 132.4, 129.9, 128.7, 128.7, 125.6, 125.1, 115.4,
10.5.
Pentafluorophenyl Benzoate (8). Yield: 82% (1.18 g). White
1
solid. H NMR (500 MHz, CDCl ): δ 8.21 (d, J = 7.5 Hz, 2H), 7.71
3
1
3
1
1
(
t, J = 7.4 Hz, 1H), 7.56 (t, J = 7.8 Hz, 2H). C{ H} NMR (126
MHz, CDCl ): δ 163.0, 142.9−142.3 (m), 141.3−140.6 (m), 139.5−
3
3
1
3
1
1
1
−
39.2 (m), 139.2−138.7 (m), 137.6−137.1 (m), 135.1, 131.1, 129.3,
1
9
27.3, 126.0−125.5 (m). F NMR (471 MHz, CDCl ): δ −152.47 to
3
3
F
152.58 (m), −158.04 (t, J = 21.7 Hz), −162.30 to −162.86 (m).
130.3, 129.5, 128.6, 125.5, 22.0, 20.2.
1
Phenyl Benzoate (9). Yield: 85% (1.68 g). White solid. H NMR
[1,1′-Biphenyl]-4-yl(p-tolyl)methanone (12g). According to
the general procedure, the reaction of 1-([1,1′-biphenyl]-4-carbonyl)-
piperidin-2-one (27.9 mg, 0.10 mmol, 1.0 equiv) and p-tolylboronic
(
500 MHz, CDCl ): δ 8.29−8.22 (m, 2H), 7.66 (t, J = 7.4 Hz, 1H),
.54 (t, J = 7.7 Hz, 2H), 7.49−7.44 (m, 2H), 7.34−7.29 (m, 1H),
3
7
1
0462
J. Org. Chem. 2021, 86, 10455−10466