Jiang et al.
5
4′-Bromo-4-(phenylsulfonyl)-[1,1′-biphenyl]-2- 8.25 (d, J=12.0Hz, 1H), 8.01 (d, J=8.0Hz, 2H), 7.72–7.65
carbonitrile (4c): White solid, yield 71%; m.p. 141°C– (m, 4H), 7.62–7.58 (m, 2H); 13C NMR (100MHz, CDCl3):
143°C; 1H NMR (400MHz, CDCl3): δ 8.31 (d, J=4.0Hz, δ 148.7, 147.3, 143.2, 142.5, 140.2, 134.4, 133.2, 131.9,
1H), 8.18 (dd, J=8.0Hz, 4.0Hz, 1H), 7.99 (d, J=8.0Hz, 131.3, 130.0, 130.0, 128.2, 124.4, 116.5, 113.0; ESI HRMS:
2H), 7.66–7.62 (m, 4H), 7.59–7.55 (m, 2H), 7.40 (d, calcd for C19H12N2O4S+Na 387.0415; found: 387.0418.
J=8.0Hz, 2H); 13C NMR (100MHz, CDCl3): δ 148.6,
3′-Nitro-4-(phenylsulfonyl)-[1,1′-biphenyl]-2-
142.0, 140.4, 135.3, 134.1, 133.1, 132.4, 131.7, 131.1, carbonitrile (4j): White solid; yield 73%; m.p. 162°C–
130.3, 129.8, 128.1, 124.7, 116.9, 112.6; ESI HRMS: calcd 164°C; 1H NMR (400MHz, CDCl3): δ 8.39–8.36 (m, 3H),
for C19H12BrNO2S+Na 419.9670; found: 419.9673.
8.26 (dd, J=8.0Hz, 4.0Hz, 1H), 8.01 (d, J=8.0Hz, 2H),
3′-Chloro-4-(phenylsulfonyl)-[1,1′-biphenyl]-2- 7.91 (d, J=8.0Hz, 1H), 7.76–7.70 (m, 2H), 7.69–7.65 (m,
carbonitrile (4d): White solid; yield 79%; m.p. 142°C– 1H), 7.62–7.58 (m, 2H); 13C NMR (100MHz, CDCl3): δ
144°C; 1H NMR (400MHz, CDCl3): δ 8.32 (d, J=4.0Hz, 148.7, 147.1, 143.1, 140.3, 138.0, 134.7, 134.4, 133.2,
1H), 8.19 (dd, J=8.0Hz, 4.0Hz, 1H), 7.99 (d, J=8.0Hz, 132.0, 131.3, 130.4, 130.0, 128.2, 124.7, 123.9, 116.5,
2H), 7.67–7.63 (m, 2H), 7.59–7.56 (m, 2H), 7.48–7.43 (m, 113.1; ESI HRMS: calcd for C19H12N2O4S+Na 387.0415;
4H); 13C NMR (100MHz, CDCl3): δ 148.2, 142.2, 140.4, found: 387.0415.
138.1, 135.1, 134.2, 133.1, 131.7, 131.2, 130.4, 130.0,
129.8, 128.8, 128.1, 127.0, 116.7, 112.8; ESI HRMS: calcd carbonitrile (4k): White solid; yield 71%; m.p. 153°C–
for C19H12ClNO2S+Na 376.0175; found: 376.0172.
155°C; 1H NMR (400MHz, CDCl3): δ 8.32 (d, J=4.0Hz,
3′,4′-Dichloro-4-(phenylsulfonyl)-[1,1′-biphenyl]-2-
3′-Bromo-4-(phenylsulfonyl)-[1,1′-biphenyl]-2- 1H), 8.20 (d, J=8.0Hz, 1H), 7.99 (d, J=8.0Hz, 2H), 7.67–
carbonitrile (4e): White solid; yield 74%; m.p. 155°C– 7.62 (m, 2H), 7.60–7.56 (m, 4H), 7.40 (d, J=12.0Hz, 1H);
1
157°C; H NMR (400MHz, CDCl3): δ 8.31 (s, 1H), 8.19 13C NMR (100MHz, CDCl3): δ 147.2, 142.6, 140.3, 136.2,
(d, J=8.0Hz, 1H), 8.00 (d, J=8.0Hz, 2H), 7.68–7.63 (m, 134.7, 134.3, 133.7, 133.2, 131.8, 131.2, 131.1, 130.7,
4H), 7.60–7.56 (m, 2H), 7.49 (d, J=8.0Hz, 1H), 7.41–7.37 129.9, 128.1, 128.0, 116.6, 112.8; ESI HRMS: calcd for
(m, 1H); 13C NMR (100MHz, CDCl3): δ 148.1, 142.2, C19H11Cl2NO2S+Na 409.9785; found: 409.9780.
140.3, 138.3, 134.1, 133.0, 132.9, 131.6, 131.5, 131.1,
130.5, 129.7, 128.0, 127.3, 123.1, 116.6, 112.8; ESI HRMS: carbonitrile (4l): White solid; yield 88%; m.p. 114°C–
calcd for C19H12BrNO2S+Na 419.9670; found: 419.9673.
116°C; 1H NMR (400MHz, CDCl3): δ 8.30 (d, J=4.0Hz,
4′-Methyl-4-(phenylsulfonyl)-[1,1′-biphenyl]-2-
2′-Chloro-4-(phenylsulfonyl)-[1,1′-biphenyl]-2- 1H), 8.15 (d, J=8.0Hz, 1H), 8.00 (d, J=8.0Hz, 2H), 7.66–
carbonitrile (4f): White solid; yield 76%; m.p. 140°C– 7.62 (m, 2H), 7.59–7.55 (m, 2H), 7.44 (d, J=8.0Hz, 2H),
142°C; 1H NMR (400MHz, CDCl3): δ 8.31 (d, J=4.0Hz, 7.31 (d, J=8.0Hz, 2H), 2.42 (s, 3H); 13C NMR (100MHz,
1H), 8.19 (dd, J=8.0Hz, 4.0Hz, 1H), 8.01 (d, J=8.0Hz, CDCl3): δ 148.9, 140.2, 139.6, 139.1, 132.9, 132.5, 132.0,
2H), 7.68–7.65 (m, 1H), 7.62–7.57 (m, 3H), 7.53 (d, 130.3, 130.0, 128.7, 128.7, 127.6, 126.9, 116.2, 111.4, 20.3;
J=8.0Hz, 1H), 7.45–7.36 (m, 2H), 7.29 (d, J=8.0Hz, 1H); ESI HRMS: calcd for C20H15NO2S+Na 356.0721; found:
13C NMR (100MHz, CDCl3): δ 147.6, 142.5, 140.3, 135.5, 356.0723.
134.2, 132.7, 132.2, 132.2, 131.1, 131.1, 130.9, 130.4,
3′-Methyl-4-(phenylsulfonyl)-[1,1′-biphenyl]-2-
129.9, 128.2, 127.3, 116.3, 114.7; ESI HRMS: calcd for carbonitrile (4m): White solid; yield 86%; m.p. 116°C–
1
C19H12ClNO2S+Na 376.0175; found: 376.0177.
118°C; H NMR (400MHz, CDCl3): δ 8.30 (s, 1H), 8.16
2′-Bromo-4-(phenylsulfonyl)-[1,1′-biphenyl]-2- (d, J=8.0Hz, 1H), 8.00 (d, J=8.0Hz, 2H), 7.67–7.63 (m,
carbonitrile (4g): White solid; yield 72%; m.p. 149°C– 2H), 7.60–7.56 (m, 2H), 7.41–7.37 (m, 1H), 7.34–7.29 (m,
1
152°C; H NMR (400MHz, CDCl3): δ 8.30 (s, 1H), 8.18 3H), 2.42 (s, 3H); 13C NMR (100MHz, CDCl3): δ 150.1,
(d, J=8.0Hz, 1H), 8.02 (d, J=8.0Hz, 2H), 7.72 (d, 141.5, 140.6, 139.0, 136.5, 134.1, 133.1, 131.5, 131.3,
J=8.0Hz, 1H), 7.69–7.65 (m, 1H), 7.62–7.58 (m, 3H), 130.7, 129.8, 129.4, 129.0, 128.0, 125.9, 117.2, 112.7, 21.5;
7.45–7.42 (m, 1H), 7.37–7.33 (m, 1H), 7.27 (d, J=8.0Hz, ESI HRMS: calcd for C20H15NO2S+Na 356.0721; found:
1H); 13C NMR (100MHz, CDCl3): δ 149.2, 142.5, 140.4, 356.0725.
137.5, 134.2, 133.6, 132.2, 132.2, 131.2, 131.1, 130.7,
129.9, 128.2, 127.9, 122.4, 116.2, 114.6; ESI HRMS: calcd carbonitrile (4n): Yellow solid; yield 85%; 132°C–134°C;
for C19H12BrNO2S+H 397.9850; found: 397.9856.
1H NMR (400MHz, CDCl3): δ 8.28 (s, 1H), 8.14 (d,
4′-Methoxy-4-(phenylsulfonyl)-[1,1′-biphenyl]-2-
4-(Phenylsulfonyl)-4′-(trifluoromethyl)-[1,1′-biphenyl]- J=8.0Hz, 1H), 7.99 (d, J=8.0Hz, 2H), 7.66–7.62 (m, 2H),
2-carbonitrile (4h): White solid; yield 66%; m.p. 147°C– 7.59–7.55 (m, 2H), 7.50 (d, J=4.0Hz, 2H), 7.02 (d,
1
149°C; H NMR (400MHz, CDCl3): δ 8.34 (s, 1H), 8.22 J=8.0Hz, 2H), 3.86 (s, 3H); 13C NMR (100MHz, CDCl3):
(d, J=8.0Hz, 1H), 8.00 (d, J=8.0Hz, 2H), 7.77 (d, δ 161.1, 149.7, 140.9, 140.7, 134.0, 133.3, 131.5, 131.0,
J=8.0Hz, 2H), 7.68–7.64 (m, 4H), 7.60–7.57 (m, 2H); 13C 130.3, 129.8, 128.7, 128.0, 117.5, 114.7, 112.3, 55.6; ESI
NMR (100MHz, CDCl3): δ 148.2, 142.7, 140.4, 134.3, HRMS: calcd for C20H15NO3S+Na 372.0670; found:
133.2, 131.8, 131.3, 129.9, 129.3, 128.1, 126.2, 116.7, 372.0673.
113.0; ESI HRMS: calcd for C20H12F3NO2S+H 388.0619;
3′,4′-Dimethoxy-4-(phenylsulfonyl)-[1,1′-biphenyl]-2-
carbonitrile (4o): Yellow solid; yield 80%; m.p. 139°C–
found: 388.0610.
4′-Nitro-4-(phenylsulfonyl)-[1,1′-biphenyl]-2- 141°C; 1H NMR (400MHz, CDCl3): δ 8.29 (d, J=4.0Hz,
carbonitrile (4i): White solid; yield 69%; m.p. 162°C– 1H), 8.14 (d, J=12.0Hz, 1H), 7.99 (d, J=8.0Hz, 2H),
164°C; 1H NMR (400MHz, CDCl3): δ 8.39–8.35 (m, 3H), 7.67–7.62 (m, 2H), 7.59–7.55 (m, 2H), 7.12 (d, J=8.0Hz,