Table 28 Copper-mediated coupling of N- and O-containing compounds with arylboronic acids
using the generalized conditions
a
R
1
B
OH
OH
+
R XH
X = N, O
CH 2 Cl 2 , rt, 24 h
2.6 equiv base
4 Ä mol. sieves
X
R
1
R
X - N, O
Cu
Entry
Starting
material
R
1
Product
Isolated
yield (%)
H
N
H
N
H
N
H
N
H
N
H
N
O N
O
O
Cl
N
H
O
N
O
N
O
H
N
O
O
O
O
HO
I
OMe
MeO
O
N
H
O
54
48
66
b
93
b
78
54
b
55
b
0
0
75
b
56
b,c
83
b,c
67
c
50
c
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
NH 2
NH 2
NH 2
NH 2
NH 2
NH 2
O
Cl
N
H
O
H
N
O
NH 2
HO
OH
I
OH
OMe
OH
OH
MeO
O
N
H
O
O NH
O
N
H
O
1
2
3
4
5
6
7
8
9
10
11
12
13
14
H
H
a
All reactions were run using 1.5 equiv of catalyst, 3 equiv of arylboronic acid, and NEt 3 as the
base
b
Recycled catalyst
c
Performed with 4 equiv of boronic acid
154
M.L. Kantam et al.