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Scale-up experiment (f). Iodobenzene (4 mmol), SOM
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7.39 (m, 2H), 7.31–7.23 (m, 2H), 7.00 (dd, J ¼ 8.3, 2.5 Hz, 1H),
3.94 (s, 3H); 13C NMR (101 MHz, chloroform-d) d 159.9, 142.7,
141.0, 129.7, 128.7, 127.4, 127.1, 119.6, 112.8, 112.6, 77.4, 77.0,
76.6, 55.2.
(10 mol%), tBuOK (12 mmol), and benzene (30 mL) were
successively placed in a 60 mL stainless steel reaction still,
which was sealed tightly and then heated to 100 ꢀC. Aer
reacting for 24 h, the reaction mixture was cooled to room
temperature. The yield was determined by column chromatog-
raphy using petroleum ether/ethyl acetate as the eluent.
4-Methoxy-1,10-biphenyl (2j).65 1H NMR (400 MHz,
chloroform-d) d 7.53 (tt, J ¼ 9.6, 2.3 Hz, 4H), 7.40 (t, J ¼ 7.7 Hz,
2H), 7.33–7.26 (m, 1H), 7.00–6.93 (m, 2H), 3.83 (s, 3H); 13C NMR
(101 MHz, chloroform-d) d 159.1, 140.8, 133.8, 128.7, 128.1,
126.7, 126.6, 114.2, 55.3.
4-(Triuoromethyl)-1,10-biphenyl (2k).34 1H NMR (400 MHz,
4.5 NMR characterization of products
Spectroscopic data of all products are exhibited as follows. All chloroform-d) d 7.68 (s, 4H), 7.61–7.56 (m, 2H), 7.49–7.43 (m,
the products gave satisfactory spectroscopic values and were 2H), 7.43–7.36 (m, 1H); 13C NMR (101 MHz, chloroform-d)
analogous to spectroscopic data in previous literature reports.
d 144.7, 139.8, 129.0, 128.2, 127.4, 127.3, 125.7, 125.7.
1,10-Biphenyl (2a).65 1H NMR (400 MHz, chloroform-d)
[1,10-Biphenyl]-4-carbonitrile (2l).65 1H NMR (400 MHz,
d 7.61–7.54 (m, 4H), 7.41 (dd, J ¼ 8.3, 6.9 Hz, 4H), 7.36–7.27 chloroform-d) d 7.90–7.84 (m, 2H), 7.77–7.72 (m, 2H), 7.62–7.56
(m, 2H); 13C NMR (101 MHz, chloroform-d) d 141.2, 128.7, (m, 2H), 7.49–7.42 (m, 2H), 7.39–7.32 (m, 1H); 13C NMR (101
127.2, 127.1.
MHz, chloroform-d) d 141.0, 140.6, 132.6, 129.0, 127.7, 127.6,
2-Methyl-1,10-biphenyl (2b).65 1H NMR (400 MHz, 127.1, 118.5, 110.3.
chloroform-d) d 7.42–7.36 (m, 2H), 7.31 (td, J ¼ 6.4, 5.7, 2.5 Hz,
N,N-Dimethyl-[1,10-biphenyl]-4-amine (2m).67 1H NMR (400
3H), 7.27–7.20 (m, 4H), 2.26 (s, 3H); 13C NMR (101 MHz, MHz, chloroform-d) d 7.61–7.55 (m, 2H), 7.48–7.38 (m, 4H),
chloroform-d) d 141.9, 135.3, 130.3, 129.8, 129.1, 128.0, 127.2, 7.36–7.29 (m, 1H), 6.84–6.78 (m, 2H), 3.02 (s, 6H); 13C NMR (101
126.7, 125.7, 20.4.
MHz, chloroform-d) d 151.0, 140.8, 132.2, 128.9, 127.7, 127.3,
3-Methyl-1,10-biphenyl (2c).65 1H NMR (400 MHz, 127.1, 112.5, 40.3.
chloroform-d) d 7.59–7.55 (m, 2H), 7.40 (dt, J ¼ 9.7, 7.7 Hz, 4H),
4-(Triuoromethoxy)-1,10-biphenyl (2n).68 1H NMR (400 MHz,
7.32 (td, J ¼ 7.5, 1.4 Hz, 2H), 7.15 (d, J ¼ 7.4 Hz, 1H), 2.41 (s, 3H); chloroform-d) d 7.58 (t, J ¼ 1.6 Hz, 1H), 7.58–7.50 (m, 3H), 7.46–
13C NMR (101 MHz, chloroform-d) d 141.3, 141.2, 138.3, 128.7, 7.38 (m, 4H), 7.38–7.30 (m, 1H); 13C NMR (101 MHz,
128.6, 128.0, 127.9, 127.2, 127.1, 124.3, 21.5.
chloroform-d) d 150.2, 150.1, 140.6, 134.1, 129.4, 128.7, 127.8,
4-Methyl-1,10-biphenyl (2d).65 1H NMR (400 MHz, 127.3, 122.0, 121.9, 121.6, 119.5.
chloroform-d) d 7.56 (dd, J ¼ 8.2, 1.4 Hz, 2H), 7.51–7.44 (m, 2H),
4-Isopropyl-1,10-biphenyl (2o).68 1H NMR (400 MHz,
7.40 (dd, J ¼ 8.3, 6.9 Hz, 2H), 7.33–7.26 (m, 1H), 7.22 (d, J ¼ chloroform-d) d 7.61–7.52 (m, 4H), 7.46–7.39 (m, 2H), 7.36–7.29
7.8 Hz, 2H), 2.37 (s, 3H); 13C NMR (101 MHz, chloroform-d) (m, 3H), 2.93 (m, 1H), 1.28 (d, J ¼ 6.8 Hz, 6H); 13C NMR (101
d 141.1, 138.3, 137.0, 129.5, 128.7, 127.0, 126.9, 21.1.
MHz, chloroform-d) d 146.5, 140.6, 138.8, 128.9, 127.7, 127.3,
2-Fluoro-1,10-biphenyl (2e).45 1H NMR (400 MHz, chloroform- 127.1, 126.6, 33.9, 23.9.
d) d 7.54 (dd, J ¼ 7.2, 1.7 Hz, 2H), 7.41 (dt, J ¼ 7.6, 5.7 Hz, 3H),
4-(tert-Butyl)-1,10-biphenyl (2p).65 1H NMR (400 MHz,
7.38–7.32 (m, 1H), 7.28 (tdd, J ¼ 7.3, 4.9, 1.8 Hz, 1H), 7.20–7.09 chloroform-d) d 7.60–7.56 (m, 2H), 7.55–7.50 (m, 2H), 7.48–7.44
(m, 2H); 13C NMR (101 MHz, chloroform-d) d 161.0, 158.5, (m, 2H), 7.41 (dd, J ¼ 8.4, 7.0 Hz, 2H), 7.36–7.27 (m, 1H), 1.36 (s,
135.8, 130.8, 130.7, 129.0, 129.0, 128.9, 128.8, 128.4, 127.6, 9H); 13C NMR (101 MHz, chloroform-d) d 150.2, 141.0, 138.3,
124.3, 124.3, 116.2, 116.0.
128.7, 127.0, 126.9, 126.8, 125.7, 34.5, 31.4.
3-Fluoro-1,10-biphenyl (2f).45 1H NMR (400 MHz, chloroform-
1-([1,10-Biphenyl]-4-yl)ethan-1-one (2q).66 1H NMR (400 MHz,
d) d 7.57–7.52 (m, 2H), 7.45–7.40 (m, 2H), 7.35 (qd, J ¼ 5.5, chloroform-d) d 8.14–8.02 (m, 2H), 7.77–7.64 (m, 4H), 7.57–7.21
3.8 Hz, 3H), 7.27 (dt, J ¼ 9.7, 1.9 Hz, 1H), 7.01 (ddt, J ¼ 11.3, 6.1, (m, 3H), 2.66 (t, J ¼ 3.5 Hz, 3H); 13C NMR (101 MHz, chloroform-
2.5 Hz, 1H); 13C NMR (101 MHz, chloroform-d) d 164.4, 161.9, d) d 129.1, 129.0, 128.9, 128.2, 127.3, 127.2, 127.1, 26.6.
143.5, 143.4, 139.9, 139.9, 130.2, 130.1, 128.8, 127.8, 127.1,
122.7, 122.7, 114.1, 114.1, 113.9, 113.9.
1,10:40,100-Terphenyl (2r).65 1H NMR (400 MHz, chloroform-d)
d 7.71–7.60 (m, 8H), 7.50–7.41 (m, 4H), 7.39–7.32 (m, 2H); 13C
4-Fluoro-1,10-biphenyl (2g).65 1H NMR (400 MHz, chloroform- NMR (101 MHz, chloroform-d) d 128.9, 128.1, 127.1, 26.5.
d) d 7.53 (dd, J ¼ 6.8, 2.4 Hz, 4H), 7.42 (t, J ¼ 7.6 Hz, 2H), 7.33 (t, J
3,5-Dimethyl-1,10-biphenyl (2s).64 1H NMR (400 MHz,
¼ 7.3 Hz, 1H), 7.11 (t, J ¼ 8.5 Hz, 2H); 13C NMR (101 MHz, chloroform-d) d 7.62–7.55 (m, 2H), 7.43–7.34 (m, 3H), 7.19 (d, J
chloroform-d) d 163.7, 161.2, 140.2, 137.3, 128.8, 128.7, 128.6, ¼ 1.5 Hz, 2H), 6.82 (m, 1H), 2.27 (s, 6H); 13C NMR (101 MHz,
127.2, 127.0, 115.7, 115.5.
chloroform-d) d 138.7, 137.3, 137.2, 129.3, 128.9, 128.3, 126.6,
2-Methoxy-1,10-biphenyl (2h).66 1H NMR (400 MHz, 126.3, 21.5.
chloroform-d) d 7.72–7.66 (m, 2H), 7.55 (t, J ¼ 7.8 Hz, 2H), 7.50–
2-Phenylnaphthalene (2t).65 1H NMR (400 MHz, chloroform-
7.40 (m, 3H), 7.17 (td, J ¼ 7.5, 1.1 Hz, 1H), 7.10 (dd, J ¼ 8.3, d) d 8.03–7.95 (m, 2H), 7.89 (m, 1H), 7.70 (m, 1H), 7.64–7.58 (m,
1.1 Hz, 1H), 3.91 (s, 3H); 13C NMR (101 MHz, chloroform-d) 2H), 7.56–7.46 (m, 3H), 7.45–7.41 (m, 2H), 7.41–7.33 (m, 1H);
d 156.4, 138.5, 130.8, 130.6, 129.5, 128.5, 127.9, 126.8, 120.8, 13C NMR (101 MHz, chloroform-d) d 140.8, 138.1, 133.7, 133.6,
111.2, 77.3, 77.0, 76.8, 55.4.
128.5, 128.3, 128.0, 127.9, 127.8, 127.6, 126.7, 126.3, 126.0,
3-Methoxy-1,10-biphenyl (2i).5 1H NMR (400 MHz, 125.9.
chloroform-d) d 7.76–7.64 (m, 2H), 7.53 (t, J ¼ 7.5 Hz, 2H), 7.49–
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RSC Adv., 2020, 10, 14500–14509 | 14507