Table 37 N-Arylation of various N nucleophiles 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
5
6
7
4.0
4.0
75 (70)
c
72
70
65
75
68
70
F
Amine
6
8
65
7
NH 2
H
N
H
N
6
F
B(OH) 2
4.0
Cl
H
N
6
Cl
B(OH) 2
4.5
H
N
6
B(OH) 2
5.0
H 3 COC
H
N
6
COCH 3
B(OH) 2
5.0
6
5.0
H
N
5.0
H
N
5.0
4.0
OCH 3
NH 2
Cl
7
7
H
N
OCH 3
Cl
NH 2
Cl
NH 2
t Bu
NH 2
Cl
7
9
H
N
tBu
60
7
H
N
Ph
60
10
NH 2
NH
7
CONH 2
SO 2 NH 2
12
5.0
H
N
55
O
NH
13
14
16
15
N
60
60
7
7
7
7
5.0
5.0
6.0
6.0
N
O
CONHPh
SO 2 NHPh
30
30
NH 2
H
N
Ph
60
4.0
11
7
a
Reaction conditions: amine (1 mmol), arylboronic acid (1 mmol), Cu(OAc) 2 (10 mol%), [bmim]
BF 4 (1 mL)
b
Isolated yield
c
Isolated yield after fourth cycle
164
M.L. Kantam et al.