Table 9 Cu(II)-NaY-catalyzed coupling reactions of aryl halides with imidazole
a
N
N
N
N
N
N
N
N
O
MeO
99% (30 h), X = Br
99% (20 h), X = Br
N
N
N
N
O 2 N
C
N
92%
b (20 h), X = Cl
99% (24 h), X = Cl
N
N
F 3 C
N
N
N
N
N
N
N
N
MeO
Cl
99% (24 h), X = I
99% (24 h), X = I
85% (48 h), X = Br
99% (40 h), X = I
N
N
O
95% (48 h), X = Cl
90%
b (84%)
c (36 h), X = Br
99% (36 h), X = I
97% (30 h), X = Cl
X
FG
+
N
HN
Cu(II)-NaY Zeolite
K 2 CO 3 (2 eq.)
N
FG
N
X = Cl, Br, I
(1)
(2)
(3)
(4)
(5)
(6)
(7)
(8)
(9)
(10)
(11)
(12)
a
Reaction conditions: aryl halide (1 mmol), imidazole (1.2 mmol), K 2 CO 3 (2 mmol), Cu(II)-NaY
(100 mg) in 3 mL of DMF, GC yields unless otherwise stated, and reactions times are reported in
parenthesis
b
Isolated yields
c
Isolated yield after third recycle
Table 10 N-Arylation of various nitrogen heterocycles
a
N
N
N
N
N
N
H
H
H
H
Entry
Nitrogen
hetrocycle
Product
N
N
N
N
N
N
1
2
3
4
22
99
20
99
22
99
36
99
Yield
(%) b
Yield
(%) b
X
+ Het-NH
K 2 CO 3
Cu(II)-NaY Zeolite
H 3 C
N-Het
X = Br
Time
(h)
Time
(h)
X = I
48
99
36
99
24
99
20
99
a
Reaction conditions: aryl halide (1 mmol), imidazole (1.2 mmol), K 2 CO 3 (2 mmol),
Cu(II)-NaY (100 mg) in 3 mL of DMF
b
GC yields
Recent Developments in Recyclable Copper Catalyst Systems for C–N Bond. . .
135