J. Gu, Y. Wan, H. Ma et al.
Tetrahedron 93 (2021) 132298
4.3.24. 2-Methylbenzaldehyde (3 m)
4.3.34. 1-(4-(Trifluoromethyl)phenyl)ethan-1-one (3u)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
10.24 (s, 1H),
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
8.03 (d, J ¼ 8.7 Hz,
7.79e7.73 (m, 1H), 7.52e7.41 (m, 1H), 7.39e7.29 (m, 1H), 7.27e7.16
2H), 7.70 (d, J ¼ 8.2 Hz, 2H), 2.62 (s, 3H). 13C NMR (101 MHz, CDCl3)
(m, 1H), 2.64 (s, 3H). 13C NMR (101 MHz, CDCl3)
d
192.92, 140.69,
d
197.04, 139.76, 134.48 (q, J ¼ 33.3 Hz), 128.69, 125.73 (q,
134.20, 133.74, 132.13, 131.85, 126.41, 19.67. HRMS (ESI): calcd for
J ¼ 4.0 Hz), 123.67 (q, J ¼ 273.7 Hz), 26.80. 19F NMR (376 MHz,
C8H9O [MþH]þ 121.0653, found 121.0653.
CDCl3)
d
ꢂ63.13. HRMS (ESI): calcd for C9H8OF3 [MþH]þ 189.0527,
found 189.0551.
4.3.25. 2-Methylbenzoic acid (4 m)
4
White solid, mp 104e106 ꢁC.
1H NMR (400 MHz, CDCl3)
4.3.35. 1-(Thiophen-2-yl)ethan-1-one (3v)
d
8.12e8.03 (m, 1H), 7.52e7.16 (m, 4H), 2.66 (s, 3H). 13C NMR
Light yellow liquid. 1H NMR (400 MHz, CDCl3)
d 7.70 (d,
(101 MHz, CDCl3)
d 173.25, 141.46, 133.05, 132.02, 131.68, 128.40,
J ¼ 3.7 Hz, 1H), 7.64 (d, J ¼ 4.9 Hz, 1H), 7.13 (t, J ¼ 4.3 Hz, 1H), 2.57 (s,
125.95, 22.19. HRMS (ESI): calcd for C8H9O2 [MþH]þ 137.0603,
3H). 13C NMR (101 MHz, CDCl3)
d 190.69, 144.43, 133.73, 132.44,
128.04, 26.83. HRMS (ESI): calcd for C6H7OS [MþH]þ 127.0218,
found 137.0594.
found 127.0210.
4.3.26. 3,5-Dimethylbenzaldehyde (3n)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
9.88 (s, 1H),
4.3.36. 1-(Pyridin-4-yl)ethan-1-one (3w)
7.44e7.40 (m, 2H), 7.21e7.18 (m, 1H), 2.33 (s, 6H). 13C NMR
Light yellow liquid. 1H NMR (400 MHz, CDCl3)
d
8.85e8.61 (m,
2H), 7.72e7.55 (m, 2H), 2.53 (s, 3H). 13C NMR (101 MHz, CDCl3)
(101 MHz, CDCl3)
d 192.82, 138.70, 136.47, 136.19, 127.52, 21.04.
HRMS (ESI): calcd for C9H11O [MþH]þ 135.0810, found 135.0804.
d
197.40, 151.00, 142.66, 121.24, 26.71. HRMS (ESI): calcd for C7H8NO
[MþH]þ 122.0606, found 122.0601.
4.3.27. 3,5-Dimethylbenzoic acid (4n)
White solid, mp 169e172 ꢁC. 3 1H NMR (400 MHz, CDCl3)
d
7.73
4.3.37. Propiophenone (3x)
(s, 2H), 7.24 (m, 1H), 2.37 (s, 6H). 13C NMR (101 MHz, CDCl3)
Light yellow liquid. 1H NMR (400 MHz, CDCl3)
d 8.01e7.91 (m,
d
172.83, 138.26, 135.59, 129.28, 128.01, 21.22. HRMS (ESI): calcd for
2H), 7.57e7.51 (m, 1H), 7.48e7.40 (m, 2H), 3.00 (q, J ¼ 7.2 Hz, 2H),
C9H11O2 [MþH]þ 151.0759, found 151.0755.
1.22 (t, J ¼ 7.2 Hz, 3H). 13C NMR (101 MHz, CDCl3)
d 200.91, 137.00,
132.96, 128.64, 128.06, 31.87, 8.33. HRMS (ESI): calcd for C9H11
O
[MþH]þ 135.0810, found 135.0807.
4.3.28. Acetophenone (3o)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d 7.99e7.92 (m, 2H),
7.59e7.53 (m, 1H), 7.50e7.41 (m, 4H), 2.60 (s, 3H). 13C NMR
4.3.38. Benzophenone (3y)
11
Colorless solid, mp 46e48 ꢁC.
1H NMR (400 MHz, CDCl3)
(101 MHz, CDCl3)
d 198.14, 137.02, 133.06, 128.51, 128.24, 26.58.
HRMS (ESI): calcd for C8H9O [MþH]þ 121.0653, found 121.0648.
d
7.89e7.71 (m, 4H), 7.64e7.53 (m, 2H), 7.53e7.40 (m, 4H). 13C NMR
(101 MHz, CDCl3)
d 196.77, 137.51, 132.40, 130.03, 128.24. HRMS
(ESI): calcd for C13H11O [MþH]þ 183.0810, found 183.0807.
4.3.29. 1-(4-Fluorophenyl)ethan-1-one (3p)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
7.92e7.89 (m, 2H),
7.06e7.02 (m, 2H), 2.51 (s, 3H). 13C NMR (101 MHz, CDCl3)
d
196.55,
4.3.39. 1,2-Diphenylethan-1-one (3z)
White solid, mp 55e56 ꢁC. 15 1H NMR (400 MHz, Chloroform-d)
165.75 (d, J ¼ 255.5 Hz), 133.53 (d, J ¼ 3.0 Hz), 130.95 (d, J ¼ 9.1 Hz),
115.66 (d, J ¼ 22.2 Hz), 26.58. 19F NMR (376 MHz, CDCl3)
ꢂ105.35.
d
d
8.06e8.04 (m, 2H), 7.62e7.55 (m, 1H), 7.53e7.46 (m, 2H), 7.36 (m,
HRMS (ESI): calcd for C8H8OF [MþH]þ 139.0559, found 139.0553.
2H), 7.33e7.28 (m, 3H), 4.32 (s, 2H). 13C NMR (101 MHz, CDCl3)
d
197.63, 136.60, 134.54, 133.18, 129.48, 128.69, 128.66, 128.63,
126.91, 45.53. HRMS (ESI): calcd for C14H13O [MþH]þ 197.0966,
4.3.30. 1-(4-Chlorophenyl)ethan-1-one (3q)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
7.80 (d, J ¼ 8.4 Hz,
found 197.0962.
2H), 7.34 (d, J ¼ 8.4 Hz, 2H), 2.50 (s, 3H). 13C NMR (101 MHz, CDCl3)
d
196.88, 139.55, 135.37, 129.74, 128.88, 26.61. HRMS (ESI): calcd for
4.3.40. 2,3-Dihydro-1H-inden-1-one (3aa)
C8H8OCl [MþH]þ 155.0264, found 155.0254.
Light yellow liquid. 1H NMR (400 MHz, CDCl3)
d 7.73 (d,
J ¼ 7.7 Hz, 1H), 7.63e7.50 (m, 1H), 7.49e7.40 (m, 1H), 7.39e7.28 (m,
1H), 3.22e2.99 (m, 2H), 2.76e2.53 (m, 2H). 13C NMR (101 MHz,
4.3.31. 1-(4-Bromophenyl)ethan-1-one (3r)
Colorless solid, mp 52e54 ꢁC. 11 1H NMR (400 MHz, CDCl3)
d
7.83
CDCl3)
d 207.17, 155.26, 137.17, 134.68, 127.36, 126.79, 123.79, 36.30,
25.88. HRMS (ESI): calcd for C9H9O [MþH]þ 133.0653, found
(d, J ¼ 8.5 Hz, 2H), 7.62 (d, J ¼ 8.5 Hz, 2H), 2.60 (s, 3H). 13C NMR
133.0644.
(101 MHz, CDCl3)
d 196.99, 135.73, 131.83, 129.79, 128.26, 26.52.
HRMS (ESI): calcd for C8H8OBr [MþH]þ 198.9759, found 198.9756.
4.3.41. 3,4-Dihydronaphthalen-1(2H)-one (3 ab)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
7.98 (dd, J ¼ 7.8,
4.3.32. 1-(3-Methoxyphenyl)ethan-1-one (3s)
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
7.59e7.45 (m, 2H),
1.4 Hz,1H), 7.41 (td, J ¼ 7.5,1.5 Hz,1H), 7.32e7.10 (m, 2H), 3.03e2.80
(m, 2H), 2.74e2.48 (m, 2H), 2.20e1.99 (m, 2H). 13C NMR (101 MHz,
7.37 (t, J ¼ 7.9 Hz, 1H), 7.18e7.06 (m, 1H), 3.86 (s, 3H), 2.60 (s, 3H).
13C NMR (101 MHz, CDCl3)
d
197.91, 159.69, 138.37, 129.48, 121.05,
CDCl3) d 198.30,144.46,133.35,132.53,128.75,127.06,126.55, 39.12,
29.64, 23.25. HRMS (ESI): calcd for C10H11O [MþH]þ 147.0810,
119.54, 112.22, 55.34, 26.66. HRMS (ESI): calcd for C9H11O2 [MþH]þ
found 147.0811.
151.0759, found 151.0756.
4.3.33. 1-(4-Methoxyphenyl)ethan-1-one (3t)
4.3.42. 9H-Fluoren-9-one (3ac)
2
Colorless liquid. 1H NMR (400 MHz, CDCl3)
d
7.95 (d, J ¼ 8.9 Hz,
Yellow solid, mp 81e84 ꢁC.
1H NMR (400 MHz, CDCl3)
2H), 6.95 (d, J ¼ 8.9 Hz, 2H), 3.88 (s, 3H), 2.57 (s, 3H). 13C NMR
d
7.64e7.60 (m, 2H), 7.49e7.42 (m, 4H), 7.26 (td, J ¼ 7.1, 1.6 Hz, 2H).
(101 MHz, CDCl3)
d
196.84, 163.47, 130.60, 130.30, 113.67, 55.48,
13C NMR (101 MHz, CDCl3)
d 194.01, 144.49, 134.77, 134.20, 129.15,
26.38. HRMS (ESI): calcd for C9H11O2 [MþH]þ 151.0759, found
124.37, 120.39. HRMS (ESI): calcd for C13H9O [MþH]þ 181.0653,
151.0754.
found 181.0640.
6