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. Author manuscript; available in PMC: 2008 Sep 12.
Published in final edited form as: J Org Chem. 2006 Jan 6;71(1):142–149. doi: 10.1021/jo0518809

Table 3.

Arylation of aryl chlorides with aryl aminesa

graphic file with name nihms63112f10.jpg
entry aryl chloride amine product Yield (%)b
1 graphic file with name nihms63112t1.jpg
1
graphic file with name nihms63112t2.jpg
4
graphic file with name nihms63112t3.jpg
5
83
2 graphic file with name nihms63112t4.jpg
1
graphic file with name nihms63112t5.jpg
2
graphic file with name nihms63112t6.jpg
3
92 c
3 graphic file with name nihms63112t7.jpg
1
graphic file with name nihms63112t8.jpg
6
graphic file with name nihms63112t9.jpg
7
73
4 graphic file with name nihms63112t10.jpg
1
graphic file with name nihms63112t11.jpg
8
graphic file with name nihms63112t12.jpg
9
86
5 graphic file with name nihms63112t13.jpg
1
graphic file with name nihms63112t14.jpg
10
graphic file with name nihms63112t15.jpg
11
85
6 graphic file with name nihms63112t16.jpg
1
graphic file with name nihms63112t17.jpg
12
graphic file with name nihms63112t18.jpg
13
65
7 graphic file with name nihms63112t19.jpg
1
graphic file with name nihms63112t20.jpg
14
graphic file with name nihms63112t21.jpg
15
80
8 graphic file with name nihms63112t22.jpg
1
graphic file with name nihms63112t23.jpg
16
graphic file with name nihms63112t24.jpg
17
85
9 graphic file with name nihms63112t25.jpg
1
graphic file with name nihms63112t26.jpg
18
graphic file with name nihms63112t27.jpg
19
99
10 graphic file with name nihms63112t28.jpg
1
graphic file with name nihms63112t29.jpg
20
graphic file with name nihms63112t30.jpg
21
96
11 graphic file with name nihms63112t31.jpg
1
graphic file with name nihms63112t32.jpg
22
graphic file with name nihms63112t33.jpg
23
73
12 graphic file with name nihms63112t34.jpg
1
graphic file with name nihms63112t35.jpg
24
graphic file with name nihms63112t36.jpg
25
84
13 graphic file with name nihms63112t37.jpg
1
graphic file with name nihms63112t38.jpg
26
graphic file with name nihms63112t39.jpg
27
87
14 graphic file with name nihms63112t40.jpg
1
graphic file with name nihms63112t41.jpg
28
graphic file with name nihms63112t42.jpg
29
99
15 graphic file with name nihms63112t43.jpg
1
graphic file with name nihms63112t44.jpg
30
graphic file with name nihms63112t45.jpg
31
98d
16 graphic file with name nihms63112t46.jpg
32
graphic file with name nihms63112t47.jpg
24
graphic file with name nihms63112t48.jpg
33
99
17 graphic file with name nihms63112t49.jpg
34
graphic file with name nihms63112t50.jpg
24
graphic file with name nihms63112t51.jpg
35
86
18 graphic file with name nihms63112t52.jpg
36
graphic file with name nihms63112t53.jpg
24
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37
85
a

Reaction conditions: 2-Chlorobenzoic acid (1.38 g, 8.83 mmol), 1.05 equiv. of amine, 1.0 equiv. of K2CO3, 9 mol% of Cu, 4 mol% of Cu2O, 3 mL of 2-ethoxyethanol and 130°C for 24 hours.

b

Isolated yields.

c

Na2CO3 was used as base.

d

2.0 equiv. of base were used