UPDATES
(4-nitrophenyl)(2,3,4,5-tetrahydro-[1,1’-biphenyl]-
4-yl)methanone (3ma)
naphthalen-2-yl(2,3,4,5-tetrahydro-[1,1’-biphenyl]-
4-yl)methanone (3qa)
Prepared according to the general procedure to afford yellow
Prepared according to the general procedure to afford white
°
solid in 61% yield, 93.6 mg, and melting point: 184.3–185.9 C.
solid in 68% yield, 106.1 mg, and melting point: 117.3–
1
1H NMR (400 MHz, CDCl3) δ 8.40–8.33 (m, 2H), 8.20–8.12
(m, 2H), 7.46–7.39 (m, 2H), 7.36 (dd, J=10.2, 4.8 Hz, 2H),
7.28 (s, 1H), 6.23–6.16 (m, 1H), 3.62 (tdd, J=8.0, 5.4, 2.7 Hz,
1H), 2.67–2.61 (m, 2H), 2.60–2.44 (m, 2H), 2.26–2.18 (m, 1H),
1.98–1.87 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 201.69,
150.28, 141.45, 140.87, 136.46, 129.33, 128.36, 127.08, 125.06,
123.98, 122.44, 41.96, 28.42, 27.01, 25.98. HRMS (EI): calcd
for C19H17NO3: 307.1208, found: 307.1215.
118.8 C. H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.07 (d,
°
J=8.6 Hz, 1H), 7.99 (d, J=7.9 Hz, 1H), 7.92 (dd, J=13.2,
8.5 Hz, 2H), 7.59 (dt, J=14.8, 7.0 Hz, 2H), 7.44 (d, J=7.6 Hz,
2H), 7.35 (t, J=7.3 Hz, 2H), 7.24 (s, 1H), 6.22 (s, 1H), 3.78 (s,
1H), 2.65 (s, 2H), 2.56 (dd, J=27.1, 14.2 Hz, 2H), 2.25 (d, J=
12.5 Hz, 1H), 2.01–1.90 (m, 1H). 13C NMR (101 MHz, CDCl3)
δ 203.33, 141.77, 136.34, 135.63, 133.64, 132.69, 129.87,
129.66, 128.66, 128.52, 128.40, 127.85, 126.99, 126.86, 125.12,
124.34, 123.21, 41.39, 29.01, 27.26, 26.43. HRMS (ESI): calcd
for C23H21O [M+H]: 313.1592, found: 313.1596.
(3-nitrophenyl)(2,3,4,5-tetrahydro-[1,1’-biphenyl]-
4-yl)methanone (3na)
furan-2-yl(2,3,4,5-tetrahydro-[1,1’-biphenyl]-4-yl)
methanone (3ra)
Prepared according to the general procedure to afford yellow oil
1
in 57% yield, 87.5 mg. H NMR (400 MHz, CDCl3) δ 8.80 (s,
1H), 8.42 (d, J=8.1 Hz, 1H), 8.31 (d, J=7.7 Hz, 1H), 7.70 (t,
J=7.9 Hz, 1H), 7.40 (d, J=7.6 Hz, 2H), 7.33 (t, J=7.4 Hz,
2H), 7.24 (d, J=8.2 Hz, 1H), 6.16 (s, 1H), 3.62 (dd, J=17.7,
6.0 Hz, 1H), 2.61 (s, 2H), 2.51 (dd, J=27.3, 13.9 Hz, 2H), 2.19
(d, J=13.7 Hz, 1H), 1.98–1.85 (m, 1H). 13C NMR (101 MHz,
CDCl3) δ 201.01, 148.60, 141.49, 137.56, 136.47, 133.97,
130.06, 128.38, 127.33, 127.08, 125.09, 123.20, 122.48, 41.61,
28.52, 27.01, 26.05. HRMS (ESI): calcd for C19H18NO3 [M+
H]: 308.1287, found: 308.1284.
Prepared according to the general procedure to afford white
°
solid in 67% yield, 84.5 mg, and melting point: 80.6–82.4 C.
1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.44 (d, J=7.6 Hz,
2H), 7.36 (t, J=7.6 Hz, 2H), 7.30–7.27 (m, 2H), 6.60 (dd, J=
3.4, 1.5 Hz, 1H), 6.21 (d, J=4.6 Hz, 1H), 3.43 (tdd, J=9.5,
5.4, 2.6 Hz, 1H), 2.64 (d, J=3.0 Hz, 2H), 2.61–2.42 (m, 2H),
2.21 (dd, J=11.4, 3.4 Hz, 1H), 2.00–1.87 (m, 1H). 13C NMR
(101 MHz, CDCl3) δ 192.33, 152.37, 146.38, 141.75, 136.24,
128.30, 126.89, 125.06, 122.94, 117.31, 112.24, 42.04, 28.18,
27.17, 25.91. HRMS (EI): calcd for C17H16O2: 252.1150, found:
252.1149.
(2-nitrophenyl)(2,3,4,5-tetrahydro-[1,1’-biphenyl]-
4-yl)methanone (3oa)
(2,3,4,5-tetrahydro-[1,1’-biphenyl]-4-yl)(thiophen-
2-yl)methanone (3sa)
Prepared according to the general procedure to afford yellow oil
1
in 51% yield, 78.3 mg. H NMR (400 MHz, CDCl3) δ 8.19 (d,
J=8.1 Hz, 1H), 7.75 (t, J=7.2 Hz, 1H), 7.63 (t, J=7.8 Hz,
1H), 7.41 (d, J=7.4 Hz, 1H), 7.36–7.28 (m, 4H), 7.22 (d, J=
6.8 Hz, 1H), 6.11 (s, 1H), 3.02 (d, J=10.2 Hz, 1H), 2.71–2.55
(m, 2H), 2.54–2.40 (m, 2H), 2.22 (d, J=13.0 Hz, 1H), 1.95–
1.81 (m, 1H). 13C NMR (101 MHz, CDCl3) δ 205.58, 145.78,
141.62, 137.69, 136.38, 134.33, 130.48, 128.31, 128.02, 126.97,
125.09, 124.58, 122.60, 46.62, 28.17, 27.13, 25.57. HRMS
(ESI): calcd for C19H18NO3 [M+H]: 308.1287, found:
308.1286.
Prepared according to the general procedure to afford white
°
solid in 70% yield, 93.8 mg, and melting point: 64.7–66.5 C.
1H NMR (400 MHz, CDCl3) δ 7.79 (s, 1H), 7.66 (d, J=4.3 Hz,
1H), 7.41 (d, J=7.4 Hz, 2H), 7.33 (t, J=7.4 Hz, 2H), 7.24 (d,
J=6.9 Hz, 1H), 7.16 (d, J=3.9 Hz, 1H), 6.18 (d, J=3.1 Hz,
1H), 3.44 (dd, J=14.7, 9.7 Hz, 1H), 2.61 (d, J=3.9 Hz, 2H),
2.59–2.36 (m, 2H), 2.21 (d, J=13.3 Hz, 1H), 2.01–1.87 (m,
1H). 13C NMR (101 MHz, CDCl3) δ 196.26, 143.81, 141.70,
136.26, 133.74, 131.76, 128.34, 128.19, 126.94, 125.07, 122.97,
43.09, 28.94, 27.20, 26.59. HRMS (ESI): calcd for C17H17OS
[M+H]: 269.1000, found: 269.1005.
(2-hydroxyphenyl)(2,3,4,5-tetrahydro-[1,1’-biphenyl]-
4-yl)methanone (3pa)
3-phenyl-1-(2,3,4,5-tetrahydro-[1,1’-biphenyl]-4-yl)
prop-2-en-1-one (3ta)
Prepared according to the general procedure to afford colorless
oil in 60% yield, 83.4 mg. 1H NMR (400 MHz, CDCl3) δ 12.51
(s, 1H), 7.83 (d, J=8.0 Hz, 1H), 7.48 (t, J=7.7 Hz, 1H), 7.40
(d, J=7.4 Hz, 2H), 7.33 (t, J=7.3 Hz, 2H), 7.23 (d, J=6.6 Hz,
1H), 7.01 (d, J=8.4 Hz, 1H), 6.91 (t, J=7.5 Hz, 1H), 6.17 (s,
1H), 3.69–3.55 (m, 1H), 2.61 (s, 2H), 2.58–2.40 (m, 2H), 2.17
(d, J=13.7 Hz, 1H), 1.93 (dd, J=15.5, 7.2 Hz, 1H). 13C NMR
(101 MHz, CDCl3) δ 209.53, 163.17, 141.57, 136.43, 136.36,
129.87, 128.37, 127.03, 125.08, 122.77, 118.94, 118.88, 118.45,
40.94, 28.91, 27.13, 26.47. HRMS (ESI): calcd for C19H19O2
[M+H]: 279.1385, found: 279.1383.
Prepared according to the general procedure to afford white
°
solid in 55% yield, 79.2 mg, and melting point: 111.1–112.0 C.
1H NMR (400 MHz, CDCl3) δ 7.67 (d, J=16.0 Hz, 1H), 7.59
(d, J=3.0 Hz, 2H), 7.41 (d, J=6.1 Hz, 5H), 7.33 (t, J=7.4 Hz,
2H), 7.24 (d, J=7.4 Hz, 1H), 6.90 (d, J=16.0 Hz, 1H), 6.18 (s,
1H), 3.08–2.97 (m, 1H), 2.59 (s, 2H), 2.49 (d, J=11.7 Hz, 2H),
2.20 (d, J=12.8 Hz, 1H), 1.90–1.78 (m, 1H). 13C NMR
(101 MHz, CDCl3) δ 202.54, 142.79, 141.77, 136.35, 134.65,
130.50, 128.98, 128.37, 128.32, 126.90, 125.07, 124.64, 122.97,
44.83, 27.98, 27.16, 25.61. HRMS (ESI): calcd for C21H21O
[M+H]: 289.1592, found: 289.1595.
Adv. Synth. Catal. 2021, 363, 1–12
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