Cross-Coupling of Aryl Sulfamates with Arylzinc Chlorides
2-p-Tolylnaphthalene:[16] 1H NMR (400 MHz, CDCl3): δ = 2.43 (s,
3 H), 7.26–7.34 (m, 2 H), 7.46–7.51 (m, 2 H), 7.59–7.67 (m, 2 H),
7.72–7.76 (m, 1 H), 7.82–7.94 (m, 3 H), 8.03 (s, 1 H) ppm. 13C
NMR (101 MHz, CDCl3): δ = 21.28, 125.57, 125.70, 125.91,
126.37, 127.40, 127.77, 128.28, 128.49, 129.74, 132.65, 133.87,
137.30, 138.37, 138.63 ppm.
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N,N-Dimethyl-4-(naphthalen-2-yl)aniline:[10c] 1H NMR (400 MHz,
CDCl3): δ = 3.01 (s, 6 H), 6.84 (d, J = 8.8 Hz, 2 H), 7.39–7.49 (m,
2 H), 7.64 (d, J = 8.8 Hz, 2 H), 7.73 (dd, J = 1.8, 8.5 Hz, 1 H), 7.80–
7.89 (m, 3 H), 7.97 (s, 1 H) ppm. 13C NMR (101 MHz, CDCl3): δ
= 40.73, 113.00, 124.32, 125.38, 125.46, 126.21, 127.73, 128.08,
128.11, 128.33, 129.15, 132.20, 134.04, 138.70, 150.20 ppm.
[4]
[5]
2-o-Tolylnaphthalene:[30] 1H NMR (400 MHz, CDCl3): δ = 2.31 (s,
3 H), 7.24–7.35 (m, 4 H), 7.45–7.53 (m, 3 H), 7.77 (s, 1 H), 7.83–
7.90 (m, 3 H) ppm. 13C NMR (101 MHz, CDCl3): δ = 20.68,
125.97, 125.99, 126.30, 127.52, 127.64, 127.82, 127.88, 127.93,
128.15, 130.15, 130.51, 132.42, 133.46, 135.72, 139.69, 142.00 ppm.
2-(4-Methoxyphenyl)naphthalene:[10c] 1H NMR (400 MHz, CDCl3):
δ = 3.85 (s, 3 H), 7.01 (d, J = 8.8 Hz, 2 H), 7.42–7.50 (m, 2 H),
7.65 (d, J = 8.8 Hz, 2 H), 7.70 (dd, J = 1.8, 8.6 Hz, 1 H), 7.81–7.90
(m, 3 H), 7.97 (s, 1 H) ppm. 13C NMR (101 MHz, CDCl3): δ =
55.50, 114.46, 125.16, 125.57, 125.78, 126.36, 127.76, 128.19,
128.48, 128.56, 132.46, 133.76, 133.90, 138.29, 159.39 ppm.
2-p-Tolylpyridine:[16] 1H NMR (300 MHz, CDCl3): δ = 2.38 (s, 3
H), 7.11–7.19 (m, 1 H), 7.26 (d, J = 8.0 Hz, 2 H), 7.64–7.70 (m, 2
H), 7.89 (d, J = 8.1 Hz, 2 H), 8.66 (d, J = 4.8 Hz, 1 H) ppm. 13C
NMR (75 MHz, CDCl3): δ = 21.16, 120.26, 121.83, 126.84, 129.53,
136.69, 138.97, 149.65, 157.53 ppm.
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CCDC-1402816 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
www.ccdc.cam.ac.uk/data_request/cif.
2-[4-(Trifluoromethyl)phenyl]pyridine:[29] 1H NMR (300 MHz,
CDCl3): δ = 7.27–7.31 (m, 1 H), 7.70–7.81 (m, 4 H), 8.11 (d, J =
8.2 Hz, 2 H), 8.72 (d, J = 4.6 Hz, 1 H) ppm. 13C NMR (101 MHz,
CDCl3): δ = 120.96, 123.07, 124.34 (J = 273.2 Hz), 125.79 (J =
3.8 Hz), 127.31, 130.91 (J = 33.3 Hz), 137.09, 142.81, 150.05,
155.98 ppm.
[8]
8-p-Tolylquinoline:[31] 1H NMR (400 MHz, CDCl3): δ = 2.42 (s, 3
H), 7.30 (d, J = 7.8 Hz, 2 H), 7.34–7.38 (m, 1 H), 7.54–7.60 (m, 3
H), 7.70 (dd, J = 1.5, 7.1 Hz, 1 H), 7.77 (dd, J = 1.4, 8.1 Hz, 1 H),
8.15 (dd, J = 1.8, 8.3 Hz, 1 H), 8.93 (dd, J = 1.8, 4.2 Hz, 1 H) ppm.
13C NMR (101 MHz, CDCl3): δ = 21.38, 121.00, 126.34, 127.36,
128.82, 128.85, 130.16, 130.56, 136.26, 136.72, 137.11, 141.02,
146.26, 150.27 ppm.
[9]
[10]
8-[4-(Trifluoromethyl)phenyl]quinoline:[31] 1H NMR (400 MHz,
CDCl3): δ = 7.43 (dd, J = 4.2, 8.3 Hz, 1 H), 7.59–7.63 (m, 1 H),
7.71–7.82 (m, 5 H), 7.86 (dd, J = 1.4, 8.1 Hz, 1 H), 8.21 (dd, J =
1.8, 8.3 Hz, 1 H), 8.94 (dd, J = 1.8, 4.2 Hz, 1 H) ppm. 13C NMR
(101 MHz, CDCl3): δ = 121.39, 124.57 (J = 272.7 Hz), 125.02 (J =
3.8 Hz), 126.39, 128.49, 128.87, 129.42 (J = 32.3 Hz), 130.51,
131.05, 136.49, 139.50, 143.34, 145.87, 150.60 ppm.
[11]
Acknowledgments
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Financial support from the National Natural Science Foundation
of China (NSFC) (grant number 21172208) and the National Basic
Research Program of China (grant number 2015CB856600) is
greatly acknowledged. Professor D.-Q. Wang is thanked for the
crystal-structure determination.
[14]
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