The results of amination reaction as obtained by different copper catalysts are
tabulated in Table 39.
Recyclability and stability studies were carried out for both encapsulated and
tethered copper catalysts. For encapsulated Cu(Phen)–Y catalyst, the catalyst
Table 36 N-Arylation of imides with various arylboronic acids using Cu(OAc) 2 ÁH 2 O/[bmim]
[BF 4 ] system
a
B(OH) 2
Entry
1
2
3
4
Arylboronic acid Time (h)
Yield (%)
b
Product
B(OH) 2
B(OH) 2
B(OH) 2
B(OH) 2
B(OH) 2
5
6
7
3.0
5.0
4.0
7.0
6.0
4.0
5.0
92
85
90
90
88
80
90
F 3 C
F
Cl
H 3 COC
Imine
NH
O
O
4
N
O
O
N
O
O
N
O
O
N
O
O
N
O
O
N
O
O
N
O
O
4
4
4
4
NH
O
O
5
8
5
5.0
88
Cl
CF 3
COCH 3
4
85
c
B(OH) 2
B(OH) 2
N
O
O
F
a
Reaction conditions: imide (1 mmol), arylboronic acid (1 mmol), Cu(OAc) 2 ÁH 2 O (10 mol%),
[bmim][BF 4 ] (1 mL)
b
Isolated yield
c
Isolated yield after fourth cycle
Recent Developments in Recyclable Copper Catalyst Systems for C–N Bond. . .
163