Pd(0)-Catalyzed Tandem One-Pot Reaction of Biphenyl Ketones/Aldehydes
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289.1387, found 289.1387.
118.6 ℃. H NMR (400 MHz, CDCl3) δ: 7.60 (s, 1H),
7.58 (s, 1H), 7.55 (d, J=8.4 Hz, 2H), 7.42 (t, J=7.6 Hz,
2H), 7.38-7.32 (m, 3H), 7.32-7.28 (m, 4H), 5.50 (d,
J=0.8 Hz, 1H), 5.43 (d, J=0.8 Hz, 1H); 13C NMR (100
MHz, CDCl3) δ: 148.7, 140.9, 140.7, 140.0, 133.8,
129.8, 129.0, 128.7, 128.5, 127.6, 127.2, 127.1, 114.8.
HRMS (ESI): m/z calcd for C20H16Cl [M + H] +
291.0935, found 291.0936.
4-(1-(p-Tolyl)vinyl)-4'-(trifluoromethyl)-1,1'-biphenyl
(5h)
Product 5h was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
eluent. White solid, 84% yield (142 mg). m.p. 149.8-
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151.2 ℃. H NMR (400 MHz, CDCl3) δ: 7.69 (d, J=
0.4 Hz, 4H), 7.55 (d, J=8.6 Hz, 2H), 7.44 (d, J=8.6 Hz,
2H), 7.26 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H),
5.47 (s, 2H), 2.38 (s, 3H); 13C NMR (100 MHz, CDCl3)
δ: 149.4, 144.4, 141.8, 139.1, 138.5, 137.9, 129.1, 129.0,
128.3, 127.4, 127.1, 125.9, 114.2, 21.3. HRMS (ESI):
m/z calcd for C22H18F3 [M+H]+ 339.1355, found
339.1353.
4-[1-(3-Chlorophenyl)vinyl]-1,1'-biphenyl (5n)
Product 5n was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
eluent. White solid, 53% yield (78 mg). m.p. 76.9-
77.6 ℃. 1H NMR (400 MHz, CDCl3) δ: 7.60-7.53 (m,
4H), 7.41 (t, J=7.6 Hz, 2H), 7.39-7.31 (m, 4H),
7.30-7.26 (m, 1H), 7.25-7.20 (m, 2H), 5.52 (s, 1H),
5.45 (s, 1H); 13C NMR (100 MHz, CDCl3) δ: 148.6,
143.5, 140.9, 140.7, 139.8, 134.3, 129.6, 128.9, 128.7,
128.5, 128.0, 127.5, 127.12, 127.11, 126.7, 115.4.
HRMS (ESI): m/z calcd for C20H16Cl [M + H] +
291.0935, found 291.0935.
2,4-Difluoro-4'-(1-(p-tolyl)vinyl)-1,1'-biphenyl (5i)
Product 5i was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
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eluent. Yellow liquid, 92% yield (141 mg). H NMR
(400 MHz, CDCl3) δ: 7.46-7.43 (m, 2H), 7.42-7.36
(m, 3H), 7.26 (d, J=8.0 Hz, 2H), 7.14 (d, J=8.0 Hz,
2H), 6.93-6.85 (m, 2H), 5.45 (d, J=1.2 Hz, 1H), 5.44
(d, J=1.2 Hz, 1H), 2.35 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 149.5, 141.2, 138.5, 137.7, 134.4, 134.4,
131.5, 131.4, 129.1, 128.3, 125.2, 125.0, 114.1, 111.8,
104.51, 104.49, 21.3. HRMS (ESI): m/z calcd for
C21H17F2 [M+H]+ 307.1293, found 307.1293.
4-(1-(4-Nitrophenyl)vinyl)-1,1'-biphenyl (5p)
Product 5p was obtained by flash column chroma-
tography on silica gel with PE∶DCM=10∶1 as the
eluent. White solid, 56% yield (85 mg). m.p. 135.2-
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136.1 ℃. H NMR (400 MHz, CDCl3) δ: 8.21 (d, J=
9.2 Hz, 2H), 7.63-7.58 (m, 4H), 7.54 (d, J=8.8 Hz,
2H), 7.46 (t, J=7.6 Hz, 2H), 7.39-7.35 (m, 3H), 5.69
(d, J=0.4 Hz, 1H), 5.60 (d, J=0.8 Hz, 1H); 13C NMR
(100 MHz, CDCl3) δ: 148.2, 148.1, 147.5, 141.4, 140.5,
139.1, 129.2, 129.0, 128.7, 127.7, 127.3, 127.2, 123.7,
117.3. HRMS (ESI): m/z calcd for C24H16NO2 [M+H]+
302.1176, found 302.1176.
4-(1-(3-Methoxyphenyl)vinyl)-1,1'-biphenyl (5k)
Product 5k was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
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eluent. Yellow liquid, 84% yield (121 mg). H NMR
(400 MHz, CDCl3) δ: 7.63-7.52 (m, 5H), 7.44-7.37
(m, 5H), 7.24 (t, J=8.0 Hz, 1H), 6.98-6.91 (m, 2H),
5.48 (d, J=16.8 Hz, 2H), 3.76 (s, 3H); 13C NMR (100
MHz, CDCl3) δ: 159.6, 149.6, 143.1, 140.8, 140.7,
140.4, 129.3, 128.9, 128.8, 127.5, 127.1, 127.0, 121.1,
114.5, 114.2, 113.4, 55.4. HRMS (ESI): m/z calcd for
C21H19O [M+H]+ 287.1430, found 287.1431.
1-(1-([1,1'-Biphenyl]-4-yl)vinyl)naphthalene (5q)
Product 5q was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
eluent. White solid, 80% yield (122 mg). m.p. 107.2-
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108.3 ℃. H NMR (400 MHz, CDCl3) δ: 7.85-7.78
4-(1-(2-Methoxyphenyl)vinyl)-1,1'-biphenyl (5l)
(m, 3H), 7.53 (d, J=7.2 Hz, 2H), 7.48-7.31 (m, 10H),
7.29 (d, J=7.2 Hz, 1H), 6.01 (s, 1H), 5.38 (s, 1H); 13C
NMR (100 MHz, CDCl3) δ: 147.9, 140.7, 140.5, 140.1,
139.9, 133.8, 132.0, 128.9, 128.3, 128.1, 127.44, 127.36,
127.19, 127.16, 127.1, 126.6, 126.1, 125.9, 125.6, 116.3.
HRMS (ESI): m/z calcd for C24H19 [M+H]+ 307.1481,
found 307.1481.
Product 5l was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
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eluent. Yellow liquid, 96% yield (137 mg). H NMR
(400 MHz, CDCl3) δ: 7.63-7.56 (m, 3H), 7.50 (d, J=
8.4 Hz, 2H), 7.42-7.35 (m, 5H), 7.26 (dd, J=1.6, 7.5
Hz, 1H), 7.01-6.97 (m, 1H), 6.91 (d, J=8.0 Hz, 1H),
5.78 (d, J=1.6 Hz, 1H), 5.33 (d, J=1.6 Hz, 1H), 3.63
(s, 3H); 13C NMR (100 MHz, CDCl3) δ: 157.2, 146.6,
140.9, 140.11, 140.06, 131.4, 131.1, 130.6, 129.2, 128.9,
127.3, 127.1, 126.9, 120.8, 115.5, 111.4, 55.8. HRMS
(ESI): m/z calcd for C21H19O [M+H]+ 287.1430,
found 287.1430.
2-(1-([1,1'-Biphenyl]-4-yl)vinyl)naphthalene (5r)
Product 5r was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
eluent. White solid, 55% yield (84 mg). m.p. 131.9-
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132.8 ℃. H NMR (400 MHz, CDCl3) δ: 7.81 (d, J=
9.6 Hz, 4H), 7.62 (d, J=7.2 Hz, 2H), 7.58 (d, J=8.4 Hz,
2H), 7.51 (dd, J=8.4, 1.6 Hz, 1H), 7.48-7.41 (m, 6H),
7.34 (t, J=7.2 Hz, 1H), 5.60 (d, J=3.2 Hz, 2H); 13C
NMR (100 MHz, CDCl3) δ: 149.8, 140.84, 140.76,
140.6, 139.0, 133.5, 133.1, 128.9, 128.9, 128.3, 127.9,
4-(1-(4-Chlorophenyl)vinyl)-1,1'-biphenyl (5m)
Product 5m was obtained by flash column chroma-
tography on silica gel with PE∶DCM=20∶1 as the
eluent. White solid, 60% yield (86 mg). m.p. 118.1-
Chin. J. Chem. 2017, XX, 1—8
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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